Triethylamine → HCID 178502038, compound

HRID 1823776Notes

Reaction equation

HRID 1823776 reaction equation
[CH3:1][O:2][C:3](=[O:15])[NH:4][C:5]1[NH:9][C:8]2[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:7]=2[N:6]=1.[F:16][C:17]([F:30])([F:29])[O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.C(N(CC)CC)C>CC(C)=O>[CH3:1][O:2][C:3]([NH:4][C:5]1[NH:9][C:8]2[CH:10]=[CH:11][C:12]([O:14][S:25]([C:22]3[CH:21]=[CH:20][C:19]([O:18][C:17]([F:16])([F:29])[F:30])=[CH:24][CH:23]=3)(=[O:27])=[O:26])=[CH:13][C:7]=2[N:6]=1)=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 523102p-(Trifluoromethoxy)benzenesulphonyl chlorideHCID 178502034HCID 178502034, compound

Product 1

HCID 178502038HCID 178502038, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of (5-hydroxy-1H-benzoimidazol-2-yl)-carbamic acid methyl ester (100 mg) and 4-trifluoromethoxy-benzenesulfonyl chloride (126 mg) in acetone (3 ml) was treated with triethylamine (130 μl). After stirring at ambient temperature for 4 hours, the reaction mixture was evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and heptane (1:1, v/v) to give 4-trifluoromethoxy-benzenesulfonic acid 2-methoxycarbonylamino-1H-benzoimidazol-5-yl ester (65 mg) as an off-white solid Mass spectrum: 432 [M+H]+; retention time=15.04 minutes.

Workup

  1. customthe reaction mixture was evaporated
  2. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and heptane (1:1

Sources & evidence

ORD record
ord-0fd6736189e946d485e1a37b3d0b903c
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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