Water → HCID 22250331, compound

HRID 352447Notes

Reaction equation

HRID 352447 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 22250331HCID 22250331, compoundYield 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-a7667e78f1764515a71da3c533fe41b5
Source dataset
uspto-grants-2004_06
Patent number
US06747047B2

Reaction notes

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