Methyl isothiocyanate → Ethyl 2-[[(methylamino)thioxomethyl]amino]-α-oxo-4-thiazoleacetate

HRID 325384Notes

Reaction equation

HRID 325384 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[O:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.[CH3:14][N:15]=[C:16]=[S:17]>C(OCC)C>[CH3:14][NH:15][C:16](=[S:17])[NH:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[O:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 11167Methyl isothiocyanateHCID 4356513Ethyl 2-(2-Amino-4-thiazolyl)-2-oxoacetateHCID 178473044HCID 178473044, compound

Product 1

HCID 54335615Ethyl 2-[[(methylamino)thioxomethyl]amino]-α-oxo-4-thiazoleacetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of ethyl 2-(2-amino-1,3-thiazol-4-yl)glyoxylate, which can be represented as ethyl 2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)glyoxylate, (20 g.) and methyl isothiocyanate (73 g.) was stirred for 5 hours at 90° to 95° C. After the reaction, to the reaction mixture was added diethyl ether. The precipitates were collected by filtration, washed with diethyl ether and then dried to give ethyl 2-[2-[3-(methyl)thioureido]-1,3-thiazol-4-yl]glyoxylate, which can be represented as ethyl 2-[2-[3-(methyl)thioureido]-2,3-dihydro-1,3-thiazol-4-yl]glyoxylate, (21.3 g.), mp. 121° to 123° C.

Workup

  1. customAfter the reaction
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-9392244fe88d409d9c3f5d64eab715c2
Source dataset
uspto-grants-1984_04
Patent number
US04440766

Reaction notes

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