Ethyl 2-aminothiazole-4-carboxylate → Ethyl 2-(3-(3,4-dichlorobenzyl)ureido)thiazole-4-carboxylate

HRID 1685009Notes

Reaction equation

HRID 1685009 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.CCN(C(C)C)C(C)C.[Cl:21][C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:25][N:26]=[C:27]=[O:28].[N-]=C=O>CN1C(=O)CCC1.CN(C1C=CN=CC=1)C>[Cl:21][C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:25][NH:26][C:27](=[O:28])[NH:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1

Participants

7

Reactant 4

HCID 73216Ethyl 2-aminothiazole-4-carboxylateHCID 81531DiisopropylethylamineHCID 105034IsocyanateHCID 27333681,2-Dichloro-4-(isocyanatomethyl)benzene

Product 1

HCID 86622748Ethyl 2-(3-(3,4-dichlorobenzyl)ureido)thiazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

The commercial starting material ethyl 2-aminothiazole-4-carboxylate (2 mmol) was dissolved in NMP and DIEA (1 equivalent) was added followed by addition of the 3,4-dichloro-benzyl isocyanate (1 equivalent). Add 5% DMAP. Heat at 160° C. under microwave irradiation for 30 min Added additional isocyanate reagent (1.0 eq) and microwave for another 30 minutes at 160° C. to obtain ethyl 2-(3-(3,4-dichlorobenzyl)ureido)thiazole-4-carboxylate in >90% conversion.

Sources & evidence

ORD record
ord-b8d44578a78149b5b2eac6302de7fe4c
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

Loading…