Toluene → HCID 68612000, compound

HRID 1848300Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9](O)([C:30]([F:33])([F:32])[F:31])[CH2:10][C:11]([C:13]2[CH:28]=[CH:27][C:16]([C:17]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[O:18])=[C:15]([CH3:29])[CH:14]=2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C1(C)C=CC=CC=1.C(OC(=O)C)(=O)C.C(N(CCCC)CCCC)CCC>CN(C)C1C=CN=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:30]([F:33])([F:32])[F:31])=[CH:10][C:11]([C:13]2[CH:28]=[CH:27][C:16]([C:17]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[O:18])=[C:15]([CH3:29])[CH:14]=2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

Conditions

Temperature: 30 °C

Procedure

0.78 g of 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutanoyl)-2-methyl-N-(pyridin-2-ylmethyl)benzoic acid amide, 4.3 g of toluene, 0.58 g of acetic anhydride, 20 mg of 4-dimethylaminopyridine, 0.40 g of tri-n-butylamine were fed and the mixture was stirred for 2.5 hours at 30° C. 2 ml of iced water was added to the reaction solution, and the reaction solution was concentrated under reduced pressure. The residue was passed through a column filled with silica gel, and the silica gel was washed with a small amount of 1:1 mixed solution of n-hexane:ethyl acetate. The organic phases were combined and the solvent was distilled off under reduced pressure to obtain 0.64 g of 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-methyl-N-(pyridin-2-ylmethyl)benzoic acid amide as a yellow solid.

Workup

concentrationthe reaction solution was concentrated under reduced pressure
additionfilled with silica gel
washthe silica gel was washed with a small amount of 1:1 mixed solution of n-hexane
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-4e4ea51c94e842c782d8971f12bddeb4
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952175B2

Reaction notes

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