Water → (N-Cyclopropyl-3-Trifluoromethylbenzylsulfonamido)-Acetamide

HRID 476523Notes

Reaction equation

[H-].[Na+].[CH:3]1([NH:6][S:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)(=[O:9])=[O:8])[CH2:5][CH2:4]1.Br[CH2:22][C:23]([NH2:25])=[O:24].O>CN(C)C=O>[CH:3]1([N:6]([CH2:22][C:23]([NH2:25])=[O:24])[S:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=2)(=[O:9])=[O:8])[CH2:5][CH2:4]1

Participants

Conditions

Temperature: 0 °C

Procedure

0.26 Gram of sodium hydride is added portionwise to a solution containing 2.77 g of N-cyclopropyl-3-trifluoromethylbenzylsulfonamide in 50 ml of dimethylformamide over an ice bath. The mixture is stirred 15 minutes at 0° C. and then 0.0105 moles of bromoacetamide is added dropwise with cooling. The mixture is stirred overnight at room temperature. Water is then added. This will result in the formation of a precipitate and oil. Water is continued to be added until no further precipitate or oil is formed. The mixture is cooled over an ice bath and then filtered. The filter cake is dissolved in hot cyclohexane and then recrystallized affording the title compound.

Workup

temperaturewith cooling
stirringThe mixture is stirred overnight at room temperature
customThis will result in the formation of a precipitate and oil
additionto be added until no further precipitate
customoil is formed
temperatureThe mixture is cooled over an ice bath
filtrationfiltered
dissolutionThe filter cake is dissolved in hot cyclohexane
customrecrystallized

Sources & evidence

ORD record: ord-e1587771cd064ef8a936c2856592006d
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04885027

Reaction notes

Loading…