Ethyl 2-amino-alpha-(hydroxyimino)thiazol-4-acetate

Base Information

• Chemical Name: Ethyl 2-amino-alpha-(hydroxyimino)thiazol-4-acetate
• CAS No.: 64485-82-1
• Molecular Formula: C7H9N3O3S
• Molecular Weight: 215.233
• Hs Code.: 2934.90
• European Community (EC) Number: 264-910-1,262-468-4
• DSSTox Substance ID: DTXSID801215981
• Wikidata: Q76324832
• Mol file: 64485-82-1.mol

Synonyms:64485-82-1;60845-81-0;(Z)-Ethyl 2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetate;Ethyl 2-(2-aminothiazole-4-yl)-2-hydroxyiminoacetate;Ethyl 2-amino-alpha-(hydroxyimino)thiazol-4-acetate;ethyl (Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate;ethyl (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetate;ETHYL (Z)-2-HYDROXYIMINO-2-(2-AMINOTHIAZOLE-4-YL)ACETATE;EINECS 262-468-4;EINECS 264-910-1;Ethyl 2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetate;Ethyl (Z)-2-amino-alpha-(hydroxyimino)thiazol-4-acetate;(2-Amino-thiazol-4-yl)-[(Z)-hydroxyimino]-acetic acid ethyl ester;C7-H9-N3-O3-S;EHATA;SCHEMBL95685;MLS006011392;4-Thiazoleacetic acid, 2-amino-.alpha.-(hydroxyimino)-, ethyl ester;(E)-ethyl 2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetate;DTXSID801215981;AKOS024306917;AM101077;SMR004703229;CS-0151909;D70139;A834769;A868876;4-(2-Aminothiazol-4-yl)-4-(hydroxyimino)acetic ester;Ethyl 2-(2-aminothiazole-4-yl)-2-hydroxyimino-(Z)-acetate;Ethyl (alphaZ)-2-amino-alpha-(hydroxyimino)-4-thiazoleacetate;Ethyl (Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetate;Ethyl 2-amino-alpha-(hydroxyimino)-4-thiazoleacetate, predominantly syn

Chemical Property of Ethyl 2-amino-alpha-(hydroxyimino)thiazol-4-acetate

Chemical Property:

• Appearance/Colour: light yellow to beige fine powder
• Vapor Pressure: 4.8E-08mmHg at 25°C
• Melting Point: 195-197 °C
• Refractive Index: 1.662
• Boiling Point: 426.8 °C at 760 mmHg
• PKA: 9.53±0.70(Predicted)
• Flash Point: 211.9 °C
• PSA: 126.04000
• Density: 1.56 g/cm³
• LogP: 1.04790
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 215.03646233
• Heavy Atom Count: 14
• Complexity: 246

Purity/Quality:

99% ^*data from raw suppliers

2-(2-Aminothiazole-4-yl)-2-hydroxyiminoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C(=NO)C1=CSC(=N1)N
• Isomeric SMILES: CCOC(=O)/C(=N\O)/C1=CSC(=N1)N
• Uses: Ethyl 2-amino-α-(hydroxyimino)-4-thiazoleacetate may be used in chemical synthesis.

Technology Process of Ethyl 2-amino-alpha-(hydroxyimino)thiazol-4-acetate

There total 6 articles about Ethyl 2-amino-alpha-(hydroxyimino)thiazol-4-acetate 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:

ethyl 2-(hydroxyimino)-3-oxybutyrate (66508-93-8) + thiourea (17356-08-0) → (Z)-ethyl 2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate (64485-82-1)

Guidance literature:

ethyl 2-(hydroxyimino)-3-oxybutyrate; With sulfuric acid; In methanol; ethanol; water; at 15 - 20 ℃;

thiourea; With tetrabutylammomium bromide; potassium carbonate; In methanol; at 20 - 28 ℃; for 2.5h;

Reference yield:

ethyl 2-(hydroxyimino)-3-oxybutyrate (66508-93-8) → (Z)-ethyl 2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate (64485-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1: SO₂Cl₂; glac. AcOH / 1 h / 58 - 60 °C

2: 8.9 g / N,N-dimethyl-acetamide / 3 h / 20 °C

With sulfuryl dichloride; acetic acid; In N,N-dimethyl acetamide;

DOI:10.1016/S0014-827X(03)00063-6

Reference yield:

thiourea (17356-08-0) + ethyl 4-chloro-2-hydroxyimino-3-oxo-butyrate (66338-95-2) → (Z)-ethyl 2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate (64485-82-1)

Guidance literature:

In ethanol; water; at 20 ℃; for 1h;

DOI:10.1016/0040-4020(78)89034-6

upstream raw materials:

thiourea

ethyl 4-chloro-2-hydroxyimino-3-oxo-butyrate

ethyl 2-(hydroxyimino)-3-oxybutyrate

ethyl acetoacetate

Downstream raw materials:

2-(2-Amino-1,3-thiazol-4-yl)-2-(hydroxyimino)acetic acid

ethyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tritylhydroxyimino)acetate

ethyl (2-aminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetate

(Z)-2-(2-aminothiazol-4-yl)-2-(triphenylmethoxyimino)acetic acid

Refernces

• 1、 Gonzalez, Maritza,Rodriguez, Zalua,Tolon, Blanca,Rodriguez, Juan C.,Velez, Herman,Valdes, Barbara,Lopez, Miguel A.,Fini, Adamo. "An alternative procedure for preparation of cefdinir". . p. 409 - 418. Retrieved 2007/10/03.
• 2、 -. "Cephalosporanic acid derivatives". . . Retrieved 2008/06/13.