Acetic Anhydride → HCID 22612687, compound

HRID 844105Notes

Reaction equation

HRID 844105 reaction equation
[F:1][C:2]([F:30])([F:29])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:20][NH:19][C:18]([C:21]4[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=4[F:28])=[N:17]3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[C:31](OC(=O)C)(=[O:33])[CH3:32]>C1(C)C=CC=CC=1>[C:31]([N:17]1[CH:16]([C:13]2[CH:12]=[CH:11][C:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:29])[F:30])=[CH:5][CH:6]=3)=[CH:15][CH:14]=2)[CH2:20][N:19]=[C:18]1[C:21]1[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=1[F:28])(=[O:33])[CH3:32]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178505722HCID 178505722, compound

Product 1

HCID 22612687HCID 22612687, compoundYield 7.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.5 g (3.6 mmol) of 4-(4′-trifluoromethoxy-4-biphenylyl)-2-(2,6-difluorophenyl)-4,5-dihydro-1H-imidazole (for example from Example V-1) were dissolved in 20 ml of toluene, admixed with 1.7 ml (1.84 g; 18 mmol) of acetic anhydride and boiled under reflux for 1 h. The mixture was then concentrated and the residue was recrystallized from a mixture of cyclohexane and ethyl acetate. This gave 1.07 g (65% of theory) of 1-acetyl-4-(4′-trifluoromethoxy-4-biphenylyl)-2-(2,6-difluorophenyl)-4,5-dihydro-1H-imidazole (I-7a). 0.6 g of concentration residue from the mother liquor was separated by column chromatography (silica gel; Ø=3cm, 1=30 cm; cyclohexane:ethyl acetate=5:1). 0.12 g (7% of theory) of 3-acetyl4-(4′-trifluoromethoxy-4-biphenylyl)-2-(2,6-difluorophenyl)-4,5-dihydro-3H-imidazole (I-7b) was obtained as second fraction as an oil.

Workup

  1. temperatureunder reflux for 1 h
  2. concentrationThe mixture was then concentrated
  3. customthe residue was recrystallized from a mixture of cyclohexane and ethyl acetate
  4. concentration0.6 g of concentration residue from the mother liquor
  5. customwas separated by column chromatography (silica gel; Ø=3cm, 1=30 cm; cyclohexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-811d03d1602343768939703250e4183f
Source dataset
uspto-grants-2002_04
Patent number
US06380237B1

Reaction notes

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