Ethyl bromopyruvate → 1-(4-chloro-phenyl)-2-(2-chloro-phenyl)-4-hydroxy-4,5-dihydro-1H-imidazole-4-carboxylic acid ethyl ester

HRID 857478Notes

Reaction equation

[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)=[NH:5].C([O-])(O)=O.[Na+].[CH2:23]([O:25][C:26](=[O:31])[C:27](=[O:30])[CH2:28]Br)[CH3:24]>CC(O)C>[CH2:23]([O:25][C:26]([C:27]1([OH:30])[CH2:28][N:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[C:4]([C:3]2[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=2[Cl:1])=[N:5]1)=[O:31])[CH3:24]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-chloro-N-(4-chloro-phenyl)-benzamidine (I-5a), 25.1 g, 95 mmol) and NaHCO3 (84 g, 189 mmol) in 2-propanol (473 ml) was treated with 3-bromo-2-oxo-propionic acid ethyl ester (14.3 ml, 22 g, 113 mmol). The reaction mixture was heated at 80° C. for 17 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was diluted with CH2Cl2 and the organic solution was washed with H2O, dried over MgSO4, and concentrated in vacuo to provide the product, 1-(4-chloro-phenyl)-2-(2-chloro-phenyl)-4-hydroxy-4,5-dihydro-1H-imidazole-4-carboxylic acid ethyl ester I-5b, as a dark red residue (36 g).

Workup

temperatureAfter cooling to room temperature
customthe solvent was removed in vacuo
additionThe residue was diluted with CH2Cl2
washthe organic solution was washed with H2O
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2f1d9e4edf6d44daa29d543637e26d7a
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07145012B2

Reaction notes

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