Water → 3-methyl-N-(1-methylethyl)-2-[[4-(trifluoromethoxy)benzoyl]amino]benzamide

HRID 1391643Notes

Reaction equation

HRID 1391643 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1.[NH2:15][C:16]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:17]=1[C:18]([NH:20][CH:21]([CH3:23])[CH3:22])=[O:19].C(N(CC)CC)C.O>C(Cl)Cl>[CH3:28][C:27]1[C:16]([NH:15][C:8](=[O:9])[C:7]2[CH:11]=[CH:12][C:4]([O:3][C:2]([F:14])([F:13])[F:1])=[CH:5][CH:6]=2)=[C:17]([CH:24]=[CH:25][CH:26]=1)[C:18]([NH:20][CH:21]([CH3:23])[CH3:22])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 167760932-amino-3-methyl-N-(1-methylethyl)benzamide

Product 1

HCID 222503313-methyl-N-(1-methylethyl)-2-[[4-(trifluoromethoxy)benzoyl]amino]benzamideYield 82.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(trifluoromethoxy)benzoyl chloride (0.29 g, 1.3 mmol) was added dropwise to a mixture of the aniline from Step B (0.25 g, 1.3 mmol) and triethylamine (0.13 g, 1.3 mmol) in 5 mL of methylene chloride at room temperature. After stirring for one hour the reaction was poured into water and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and evaporated under reduced pressure. The resulting solids were washed with hexane/ether and filtered to afford 0.41 g of the title compound, a compound of the present invention, as a solid melting at 207-209° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. washThe resulting solids were washed with hexane/ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-db1b314ca84d45288920b29f4f9959bf
Source dataset
uspto-grants-2008_03
Patent number
US07338978B2

Reaction notes

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