S-2-Benzothiazolyl (Z)-2-(2-aminothiazol-4-yl)-2-acetyloxyiminothioacetate

Base Information

• Chemical Name: S-2-Benzothiazolyl (Z)-2-(2-aminothiazol-4-yl)-2-acetyloxyiminothioacetate
• CAS No.: 104797-47-9
• Molecular Formula: C14H10N4O3S3
• Molecular Weight: 378.456
• Hs Code.: 2934999090
• European Community (EC) Number: 457-660-1
• DSSTox Substance ID: DTXSID901035669
• Mol file: 104797-47-9.mol

Synonyms:104797-47-9;(Z)-S-benzo[d]thiazol-2-yl 2-(acetoxyimino)-2-(2-aminothiazol-4-yl)ethanethioate;S-2-Benzothiazolyl (Z)-2-(2-aminothiazol-4-yl)-2-acetyloxyiminothioacetate;S-2-benzothiazolyl (Z)-2-(2-aminothiazol-4-yl) -2-acetyloxyiminothioacetate;[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-(1,3-benzothiazol-2-ylsulfanyl)-2-oxoethylidene]amino] acetate;EC 457-660-1;DTXSID901035669;AKOS015963308;AC-5575;(Z)-S-benzo[d]thiazol-2-yl2-(acetoxyimino)-2-(2-aminothiazol-4-yl)ethanethioate;[(E)-[1-(2-Amino-1,3-thiazol-4-yl)-2-(1,3-benzothiazol-2-ylsulfanyl)-2-oxoethylidene]amino] acetate

Chemical Property of S-2-Benzothiazolyl (Z)-2-(2-aminothiazol-4-yl)-2-acetyloxyiminothioacetate

Chemical Property:

• Vapor Pressure: 2.66E-14mmHg at 25°C
• Melting Point: 143-145℃
• Refractive Index: 1.797
• Boiling Point: 598.834 °C at 760 mmHg
• PKA: 0.48±0.10(Predicted)
• Flash Point: 315.964 °C
• PSA: 185.13000
• Density: 1.667 g/cm³
• LogP: 2.98060
• Water Solubility.: 76.6μg/L at 20℃
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 377.99150371
• Heavy Atom Count: 24
• Complexity: 533

Purity/Quality:

99% ^*data from raw suppliers

S-2-Benzothiazolyl(Z)-2-(2-Aminothiazol-4-yl)-2-acetyloxyiminothioacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)ON=C(C1=CSC(=N1)N)C(=O)SC2=NC3=CC=CC=C3S2
• Isomeric SMILES: CC(=O)O/N=C(/C1=CSC(=N1)N)\C(=O)SC2=NC3=CC=CC=C3S2

Technology Process of S-2-Benzothiazolyl (Z)-2-(2-aminothiazol-4-yl)-2-acetyloxyiminothioacetate

There total 5 articles about S-2-Benzothiazolyl (Z)-2-(2-aminothiazol-4-yl)-2-acetyloxyiminothioacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

di(benzothiazol-2-yl)disulfide (120-78-5) + (Z)-2-(2-amino-4-thiazolyl)-2-(acetoxyimino)acetic acid (110130-88-6) → S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate (104797-47-9)

Guidance literature:

With triethylamine; triphenylphosphine; In dichloromethane; at 10 - 30 ℃; for 0.5h;

DOI:10.1080/00397910701397284

Reference yield: 74.02%

di(benzothiazol-2-yl)disulfide (120-78-5) + ethyl 2-amino-α-(hydroxyimino)-4-thiazole acetate (60845-81-0) → S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate (104797-47-9)

Guidance literature:

ethyl 2-amino-α-(hydroxyimino)-4-thiazole acetate; With N,N,N'N'-tetramethyl-1,3-propanediamine; potassium tert-butylate; In acetonitrile; for 4h;

With acetic anhydride; In acetonitrile; at 25 - 40 ℃; for 1h; pH=Ca. 6.1;

di(benzothiazol-2-yl)disulfide; With triethyl phosphite; In acetonitrile; at 15 ℃; for 0.5h; pH-value; Reagent/catalyst;

Reference yield:

tri(n-butyl)ammonium syn-2-(2-aminothiazol-4-yl)-2-(methylcarbonyloxyimino)acetate + di(benzothiazol-2-yl)disulfide (120-78-5) → S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate (104797-47-9)

Guidance literature:

tri(n-butyl)ammonium syn-2-(2-aminothiazol-4-yl)-2-(methylcarbonyloxyimino)acetate; di(benzothiazol-2-yl)disulfide; In dichloromethane; at 0 ℃; for 0.0833333h;

With triethyl phosphite; In dichloromethane; at -15 - 0 ℃; for 2.33333h;

upstream raw materials:

di(benzothiazol-2-yl)disulfide

(Z)-2-(2-amino-4-thiazolyl)-2-(acetoxyimino)acetic acid

ethyl 2-amino-α-(hydroxyimino)-4-thiazole acetate

Downstream raw materials:

cefdinir

cefdinir lactone

Refernces

• 1、 -. "Cefdinir active thioester preparation method (by machine translation)". Paragraph 0032-0034; 0035-0037; 0038-0040. . Retrieved 2018/04/21.
• 2、 -. "TERTIARY AMINE SALTS OF 2-(2-AMINOTHIAZOLE-4-YL)-2-ACYLOXYIMINO)ACETIC ACID". Page/Page column 11. . Retrieved 2010/02/15.