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

HRID 890132Notes

Reaction equation

HRID 890132 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 string 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-273e5d27788643bbaa6afdafbfdfa766
Source dataset
uspto-grants-2006_02
Patent number
US06995178B2

Reaction notes

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