Phosgene → HCID 86607798, compound

HRID 2105877Notes

Reaction equation

HRID 2105877 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[NH:11][C:10]([C:20]3[C:21]([O:32][CH2:33][CH3:34])=[CH:22][C:23]([Cl:31])=[C:24]([S:26]([NH:29][CH3:30])(=[O:28])=[O:27])[CH:25]=3)=[N:9]2)=[CH:4][CH:3]=1.[C:35](Cl)([Cl:37])=[O:36].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:31][C:23]1[C:24]([S:26](=[O:28])(=[O:27])[NH:29][CH3:30])=[CH:25][C:20]([C:10]2[N:9]([C:35]([Cl:37])=[O:36])[CH:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:12]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[N:11]=2)=[C:21]([O:32][CH2:33][CH3:34])[CH:22]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 86607799HCID 86607799, compound

Product 1

HCID 86607798HCID 86607798, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In an analogous manner as described in example 29, 5-[4,5-bis-(4-chloro-phenyl)-4,5-dihydro-1H-imidazol-2-yl]-2-chloro-4-ethoxy-N-methyl-benzenesulfonamide was treated with phosgene and diisopropylethylamine in methylene chloride to give 2-(4-chloro-2-ethoxy-5-methylsulfamoyl-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dihydro-imidazole-1-carbonyl chloride. The crude carbamoyl chloride was then reacted with 1-hydroxybenzotriazole hydrate and diisopropylethylamine in methylene chloride to give the racemic 2-(4-chloro-2-ethoxy-5-methylsulfamoyl-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dihydro-imidazole-1-carboxylic acid benzotriazol-1-yl ester after purification by flash column chromatography (silica gel, eluting with a gradient of ethyl acetate in hexanes).

Sources & evidence

ORD record
ord-5790362b30534983815b17be7cb0b0c0
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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