104797-47-9

Basic information

• Product Name: S-2-BENZOTHIAZOLYL (Z)-2-(5-AMINO-1,2,4-THIADIAZOL-3-YL)-2-METHOXYIMINO THIOACETATE
• Synonyms: CAEM;S-2-BENZOTHIAZOLYL (Z)-2-(2-AMINOTHIAZOL-4-YL)-2-ACETYLOXYIMINOTHIOACETATE;ZAEM;2-(Z)-(2-AMINOTHIAZOL-4-YL)-2-ACETOXYIMINOACETIC ACID-2-BENZOTHIAZOLTHIOESTER(T15-AE);S-2-BENZOTHIAZOLYL(Z)-2-(2-AMINOTHIAZOL-4-YL)-2-ACETYLOXYIMINOTHIOACETATE (CAEM);CAEM:S-2-BENZOTHIAZOLYL ( Z ) -2-(2-AMINOTHIAZOL-4-YL)-2-ACETYLOXYIMINOTHIOACETATE;4-Thiazoleethanethioicacid, a-[(acetyloxy)iMino]-2-aMino-,S-2-benzothiazolyl ester, (aZ)-;2-Mercaptobenzothiazolyl (Z)-2-(2-amino-4-thiazolyl)-2-acetyloxyiminoacetate
• CAS NO: 104797-47-9
• Molecular Formula: C₁₄H₁₀N₄O₃S₃
• Molecular Weight: 351.43
• Mol File: 104797-47-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 143-145℃
• Boiling Point: 598.834 °C at 760 mmHg
• Flash Point: 315.964 °C
• Appearance: /
• Density: 1.66
• Vapor Pressure: 2.66E-14mmHg at 25°C
• Refractive Index: 1.797
• PKA: 0.48±0.10(Predicted)
• Water Solubility: 76.6μg/L at 20℃
• CAS DataBase Reference: S-2-BENZOTHIAZOLYL (Z)-2-(5-AMINO-1,2,4-THIADIAZOL-3-YL)-2-METHOXYIMINO THIOACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: S-2-BENZOTHIAZOLYL (Z)-2-(5-AMINO-1,2,4-THIADIAZOL-3-YL)-2-METHOXYIMINO THIOACETATE(104797-47-9)
• EPA Substance Registry System: S-2-BENZOTHIAZOLYL (Z)-2-(5-AMINO-1,2,4-THIADIAZOL-3-YL)-2-METHOXYIMINO THIOACETATE(104797-47-9)

Safety Data

• Hazardous Substances Data: 104797-47-9(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C14H10N4O3S3/c1-7(19)21-18-11(9-6-22-13(15)16-9)12(20)24-14-17-8-4-2-3-5-10(8)23-14/h2-6H,1H3,(H2,15,16)/b18-11-

Upstream product

• 120-78-5 di(benzothiazol-2-yl)disulfide 
• 110130-88-6 (Z)-2-(2-amino-4-thiazolyl)-2-(acetoxyimino)acetic acid 
• 60845-81-0 ethyl 2-amino-α-(hydroxyimino)-4-thiazole acetate 

Downstream Products

• 946573-41-7 cefdinir lactone 
• 91832-40-5 cefdinir 

Relevant articles and documents

Method for producing cefdinir active ester

The invention relates to a method for producing cefdinir active ester, and belongs to the technical field of medicine synthesis. The preparation method comprises the following steps: by taking ethyl demethylaminothioxime acid as a raw material, dissolving the ethyl demethylaminothioxime acid by utilizing organic alkali and an inert solvent, reacting, cooling, adding acetic anhydride, and continuously reacting, so as to obtain an acetylated organic amine salt solution of the demethylaminothioxime acid; dropwise adding phosphite, and adding DM by controlling the feeding time to obtain a crude product; dissolving the crude product, and crystallizing to obtain the cefdinir active ester. According to the invention, the processes of aqueous-phase acid formation and crystal water removal in the traditional process are prevented, and no waste salt or waste water is generated; the organic base serves as a hydrolytic agent and an esterification catalyst, the use amount of the ester catalyst is reduced, and the cefdinir active ester with the purity of 99.40% or above can be obtained through a DMF/ROH elution method.

Improved synthesis of Cefdinir and its polymorphic form, an antibacterial active pharmaceutical ingredient

New methods for the preparation of Cefdinir 1 and its polymorphic form Sesqui hydrate 1a are described. The synthesis of 2-mercaptobenzothiazolyl (Z)-2-(2-amino-4-thiazolyl)-2-acetoxyiminoacetate 4 was affected by using triphenylphosphine and triethylamine, and acylation of 7-amino-3-vinylcephem-4- carboxylic acid 5 followed by deprotection with K2CO3 in the presence of ammonium chloride in the same pot yielded crude Cefdinir. Purification of crude Cefdinir through resin and treatment of the resulting wet product with trifluoroacetic acid gave highly pure TFA salt of Cefdinir 6, which on neutralization afforded 1a in excellent yield. The impurity profiling of this compound has also been discussed. Copyright Taylor & Francis Group, LLC.

TERTIARY AMINE SALTS OF 2-(2-AMINOTHIAZOLE-4-YL)-2-ACYLOXYIMINO)ACETIC ACID

Subject of the present invention are crystalline tertiary amine salts of 2-(2-aminothiazole-4-yl)-2-(acyloxyimino)acetic acid compounds of formula (I) wherein R1, R2 and R3 independently represents unsubstituted or substituted alkyl, cyclo-alkyl or aryl, and R4 denotes acyl, which may be obtained in anhydrous form. Crystalline compounds of formula I are useful in a reaction step with an activating agent in order to produce cefdinir. Additionally, a process to prepare compounds of formula I is a part of the present invention.