Toluene → HCID 66738433, compound

HRID 1848298Notes

Reaction equation

HRID 1848298 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](O)([C:23]([F:26])([F:25])[F:24])[CH2:10][C:11]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[C:15]([CH3:22])[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(CC)CC)C>CN(C)C1C=CN=CC=1.Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:23]([F:26])([F:24])[F:25])=[CH:10][C:11]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[C:15]([CH3:22])[CH:14]=2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68612341HCID 68612341, compound

Product 1

HCID 66738433HCID 66738433, compoundYield 69.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

0.48 g of 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutanoyl)-2-methylbenzoic acid amide, 1.5 g of toluene, 0.23 g of acetic anhydride, 27 mg of 4-dimethylaminopyridine and 0.23 g of triethylamine were fed and the mixture was stirred for 2.5 hours at 30° C. 2 ml of iced water and 2 drops of concentrated hydrochloric acid were added to the reaction solution, and the deposited solid was collected by filtration. The solid was washed with a small amount of toluene and distilled water, and dried under reduced pressure. 0.32 g of 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-methylbenzoic acid amide was obtained as a flesh color solid.

Workup

  1. filtrationthe deposited solid was collected by filtration
  2. washThe solid was washed with a small amount of toluene
  3. distillationdistilled water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-7b18b3e9249d4007bcbeee8b1dd08d10
Source dataset
uspto-grants-2015_02
Patent number
US08952175B2

Reaction notes

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