80756-85-0

80756-85-0 - Names and Identifiers

Name	2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetic,thiobenzothiazole ester
Synonyms	MAEM Ceftriaxone Sodium intermediate S-2-BENZATHIAZOYL-2-AMINO-ALPHA-METHOXYIMINO-4-THIAZOLACETAT S-2-BENZOTHIAZOYL-2-AMINO-ALPHA-METHOXYIMINO-4-THIAZOLEACETATE s-2-benzothiazoyl-2-amino-alpha-methoxyimino-4-thiazoleacetate 2-Mercaptobenzothiazolyl (2-Aminothiazolyl)-Methoxyimino Acetate 2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetic,thiobenzothiazole ester S-(Benzothiazol-2-yl) 2-amino-α-(methoxyimino) thiazole-4-thioacetate S-2-Benzothiazolyl 2-amino-alpha-(methoxyimino)-4-thiazolethiolacetate (2-mercaptobenzothiazolyl)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate 2-MERCAPTOBENZOTHIAZOLYL(Z)-2-AMINOTHIAZOLE-4-YL-2-METHOXY IMINO ACETATE Benzothiazol-2-yl (Z)-2-methoxyimino-2-(2-aminothiazole-4-yl)thioacetate 2-amino-alpha-(methoxyimino)-4-thiazoleethanethioic aci s-2-benzothiazolyl S-(Benzothiazol-2-yl) (Z)-(2-aminothiazol-4-yl) (methoxyimino) thioacetate s-2-benzothiazolyl (z)-2-amino-alpha-(methoxyimino)-4thiazoleethanethioate (BENZOTHIAZOL-2-YL)-2-(2-AMINOTHIZAZOL-4-YL)-(Z)-2-METHOXYIMINO THIOACETATE (Benzothiazol-2-yl)-2-(2-amino-thiazol-4-yl)-(z)-2-methoxyimino Thioacetate (2-mercaptobenzothiazolyl)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate(syn s-benzothiazol-2-yl (z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)thioacet 2-Amino-α-(methoxyimino)-4-thiazoleethanethioic acid, S-2-benzothiazolyl ester S-1,3-benzothiazol-2-yl (2E)-(2-amino-1,3-thiazol-4-yl)(methoxyimino)ethanethioate S-1,3-benzothiazol-2-yl (2Z)-(2-amino-1,3-thiazol-4-yl)(methoxyimino)ethanethioate
CAS	80756-85-0 84994-24-1
EINECS	279-540-6
InChI	InChI=1/C13H10N4O2S3/c1-19-17-10(8-6-20-12(14)15-8)11(18)22-13-16-7-4-2-3-5-9(7)21-13/h2-6H,1H3,(H2,14,15)/b17-10-
InChIKey	COFDRZLHVALCDU-YVLHZVERSA-N

80756-85-0 - Physico-chemical Properties

Molecular Formula	C13H10N4O2S3
Molar Mass	350.43
Density	1.63
Melting Point	128-130°C(lit.)
Boling Point	563.2±42.0 °C(Predicted)
Flash Point	294.4°C
Solubility	Chloroform (Slightly), Methanol (Slightly)
Vapor Presure	1.04E-12mmHg at 25°C
Appearance	Solid
Color	Pale Yellow
pKa	1.22±0.10(Predicted)
Storage Condition	Refrigerator, Under Inert Atmosphere
Stability	Moisture Sensitive
Refractive Index	1.6200 (estimate)
MDL	MFCD00129148
Physical and Chemical Properties	Appearance: light yellow crystalline powder Melting Point: 126~132 ℃
Use	For the manufacture of cefotaxime, ceftriaxone, ceftriaxone, cefetamet pivoxil and other pioneering drugs

80756-85-0 - Risk and Safety

Hazard Symbols	Xi - Irritant
Risk Codes	36/37/38 - Irritating to eyes, respiratory system and skin.
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection
WGK Germany	2
RTECS	XJ4664500

80756-85-0 - Upstream Downstream Industry

Raw Materials

Accelerator (DM)
Dichloromethane
Triphenylphosphine
Triethylamine

80756-85-0 - Reference Information

Introduction	AE-active ester, the chemical name 2-methoxyimino-2-(2-amino-4-thiazolyl)-(z)-thioacetic acid benzothiazolyl ester. Appearance white or light yellow crystalline powder, melting point 128130°C. Low toxicity, bitter, soluble in acetone, Tetrahydrofuran, acetonitrile-soluble, methylene chloride, insoluble in water, and flame can burn.
Application	AE-active ester is one of the important side chains of semi-synthetic cephalosporin antibiotics, ceftriaxone sodium, cefpirome, cefpirome and other third and fourth generation semi-synthetic cephalosporin essential intermediates. AE-active esters are Ester derivatives, which can be used as the main raw materials for the production of ceftriaxone, cefotaxime sodium and other drugs.
preparation	in a ml Four-necked flask equipped with mechanical stirring, constant pressure dropping funnel, reflux condenser and thermometer, add 20g(0.0995mol) of ammoniacal acetic acid, add dibenzothiazole sulfide, pyridine and 100ml of dichloromethane in proportion, turn on stirring, slowly add 80ml of dichloromethane solution of triphenylphosphorus Dropwise under vigorous stirring at room temperature, after the addition, the reaction was stirred at a temperature of 20 to 25 ° C. For 3H (t1), cooled in an ice bath, filtered, and the filter cake was washed with methanol and dried under vacuum, AE-active ester 29.1g(0.08314mol, theoretical 0.0995mol) was obtained with a yield of 83.6% and a content of 98.6%(LC). The filtrate was slowly added dropwise with vigorous stirring. 50ml dichloromethane solution of carbonate was added, and the reaction was continued at 20~25 °c for 3 hours (t2). After the reaction was finished, the filter was filtered, and the filter cake was washed with methanol, dibenzothiazole sulfide 16.6g(0.05mol, the theoretical value is the sum of the recovered amount and the amount not taking part in the reaction, here should be 0.0995 × 1.2-0.0995 0 No. 0995/2=0.07mol), the yield is 71.43%, the content is 98.1%(LC), the filtrate is concentrated, methanol recrystallization, triphenylphosphine 22.9g(0.0874mol, the theoretical value is 0.1194mol), the yield was about 73.2% and the content was 98.3%(LC).
Use	for the manufacture of cefotaxime, ceftriaxone, cefetamet pivoxil

Last Update：2024-04-09 18:58:34

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