p-Toluenesulfonic acid monohydrate → 5-bromo-2-neopentyl-1-(2-(trifluoromethoxy)ethyl)-1H-benzo[d]imidazole

HRID 1817900Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:16][CH2:17][CH2:18][O:19][C:20]([F:23])([F:22])[F:21])=[C:6]([NH:8][C:9](=O)[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:7]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:16]([CH2:17][CH2:18][O:19][C:20]([F:23])([F:22])[F:21])[C:9]([CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:8][C:6]=2[CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of N-(5-bromo-2-[2-(trifluoromethoxy)ethyl]amino]phenyl)-3,3-dimethylbutanamide (step C, 728 mg, 1.83 mmol) and p-toluenesulfonic acid monohydrate (350 mg, 1.83 mmol) in toluene (20 mL) was stirred at 120° C. for 8 h. Then, the mixture was allowed to cool to room temperature overnight to afford crystalline precipitates. The precipitates were collected by filtration, and dissolved in ethyl acetate and saturated sodium hydrogencarbonate aqueous solution. The organic layer was separated, washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to afford the title compound (555 mg, 80%) as an amber solid.

Workup

temperatureto cool to room temperature overnight
customto afford crystalline precipitates
filtrationThe precipitates were collected by filtration
dissolutiondissolved in ethyl acetate
customThe organic layer was separated
washwashed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-356b22fdcf6b429a8f70c935e95cea0f
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598393B2

Reaction notes

Loading…