Triethylamine → HCID 18515909, compound

HRID 1369515Notes

Reaction equation

HRID 1369515 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:23])=[C:6]([NH:8][C:9](=[O:22])[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH3:21])=[CH:12][CH:11]=2)[CH:7]=1.C(N(CC)CC)C.[F:31][C:32]([F:43])([F:42])[C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][CH:41]=1)[C:36](Cl)=[O:37]>C(Cl)Cl>[CH3:23][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:36](=[O:37])[C:35]2[CH:39]=[CH:40][CH:41]=[C:33]([C:32]([F:31])([F:42])[F:43])[CH:34]=2)=[CH:7][C:6]=1[NH:8][C:9](=[O:22])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH3:21])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 22291090HCID 22291090, compound

Product 1

HCID 18515909HCID 18515909, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(5-amino-2-methylphenyl)-4-(2-ethoxyethoxy)benzamide (0.141 g) and triethylamine (0.121 g) in methylene chloride (5 ml) was added to 3-trifluoromethylbenzoyl chloride (0.104 g) and the resultant mixture was stirred at ambient temperature for 18 hours. The mixture was washed in turn with a 1M aqueous citric acid solution, a saturated aqueous sodium bicarbonate solution and water. The organic solution was evaporated and the residue was triturated under a mixture of diethyl ether and ethyl acetate. The resultant solid was isolated and dried under vacuum. There was thus obtained the title compound (weight 0.042 g); Mass Spectrum: M+H+ 487.

Workup

  1. washThe mixture was washed in turn with a 1M aqueous citric acid solution
  2. customThe organic solution was evaporated
  3. customthe residue was triturated under a mixture of diethyl ether and ethyl acetate
  4. customThe resultant solid was isolated
  5. customdried under vacuum

Sources & evidence

ORD record
ord-817cd2f180494fe6aff6c7aed1466174
Source dataset
uspto-grants-2003_06
Patent number
US06579872B1

Reaction notes

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