Ethanol → Ethyl 2-(2-aminothiazol-4-yl)-2-(2-chloroethoxyimino)acetate

HRID 848288Notes

Reaction equation

HRID 848288 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][N:5]=[C:6]([C:12](=O)[CH2:13]Cl)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[NH2:16][C:17]([NH2:19])=[S:18].O.O.O.C([O-])(=O)C.[Na+].C(O)C>O>[NH2:19][C:17]1[S:18][CH:13]=[C:12]([C:6](=[N:5][O:4][CH2:3][CH2:2][Cl:1])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:16]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 2723790ThioureaHCID 23665404Sodium Acetate TrihydrateHCID 54169228Ethyl 2-(2-chloroethoxyimino)-3-oxo-4-chlorobutyrate

Product 1

HCID 53650816Ethyl 2-(2-aminothiazol-4-yl)-2-(2-chloroethoxyimino)acetateYield 45.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-(2-chloroethoxyimino)-3-oxo-4-chlorobutyrate (syn isomer, 68 g.), thiourea (20.2 g.), sodium acetate trihydrate (36.2 g.), ethanol (270 ml.) and water (170 ml.) were treated in a similar manner to that of Example F-(3) to give ethyl 2-(2-aminothiazol-4-yl)-2-(2-chloroethoxyimino)acetate (syn isomer, 33.7 g.), mp 126° to 128° C.

Sources & evidence

ORD record
ord-21273b1437d54c01956ef7db82ca7cbe
Source dataset
uspto-grants-1981_10
Patent number
US04294960

Reaction notes

Loading…