Potassium Carbonate → 6-Chloro-3-{2-[3-(3-chloro-2-methyl-phenyl)-4-oxo-imidazolidin-1-yl]-2-oxo-ethyl}-3H-benzooxazol-2-one

HRID 1710674Notes

Reaction equation

Cl[CH2:2][C:3]([N:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=2[CH3:18])[CH2:6]1)=[O:4].[Cl:19][C:20]1[CH:29]=[CH:28][C:23]2[NH:24][C:25](=[O:27])[O:26][C:22]=2[CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Cl:19][C:20]1[CH:29]=[CH:28][C:23]2[N:24]([CH2:2][C:3]([N:5]3[CH2:9][C:8](=[O:10])[N:7]([C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=4[CH3:18])[CH2:6]3)=[O:4])[C:25](=[O:27])[O:26][C:22]=2[CH:21]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of (2-chloro-acetyl)-3-(3-chloro-2-methyl-phenyl)-imidazolidin-4-one (76) (28.6 mg, 1 equiv), 6-Chloro-3H-benzooxazol-2-one (16.9 mg, 1 equiv) and potassium carbonate (27 mg, 2 equiv) in DMF (2 ml) was stirred at 60° C. overnight, diluted with ethyl acetate, washed with water, purified with HPLC to give 6-chloro-3-{2-[3-(3-chloro-2-methyl-phenyl)-4-oxo-imidazolidin-1-yl]-2-oxo-ethyl}-3H-benzooxazol-2-one (77): LCMS observed for (M+H)+: 421.2.

Workup

washwashed with water
custompurified with HPLC

Sources & evidence

ORD record: ord-eafef0df97b64dcbb8f661292d81896c
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790726B2

Reaction notes

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