3-(Trifluoromethyl)aniline → HCID 19354604, compound

HRID 377553Notes

Reaction equation

HRID 377553 reaction equation
[F:1][CH:2]([F:22])[C:3]1[O:8][CH2:7][N:6]([C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=O)[C:5](=[O:15])[C:4]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[NH2:36][C:37]1[CH:38]=[C:39]([C:43]([F:46])([F:45])[F:44])[CH:40]=[CH:41][CH:42]=1>ClCCl.CN(C)C=O>[F:44][C:43]([F:45])([F:46])[C:39]1[CH:38]=[C:37]([NH:36][C:10](=[O:12])[C:9]([N:6]2[C:5](=[O:15])[C:4]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[C:3]([CH:2]([F:1])[F:22])[O:8][CH2:7]2)([CH3:13])[CH3:14])[CH:42]=[CH:41][CH:40]=1

Participants

7

Reactant 4

HCID 73753-(Trifluoromethyl)anilineHCID 8471Triethylamine2×HCID 65578Oxalyl chlorideHCID 19354606HCID 19354606, compound

Product 1

HCID 19354604HCID 19354604, compoundYield 26.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 2-(6-difluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoic acid (0.70g) in dichloromethane was added oxalylchloride (0.22 ml) followed by 1 drop of dimethylformamide. The reaction mixture was stirred at ambient temperature for 30 minutes and then cooled to 0° C. To the solution was added in turn triethylamine (0.36 ml), 3-aminobenzotrifluoride (0.34 g) and then triethylamine (0.36 ml). The reaction mixture was stirred at 0° C. for 30 minutes and at ambient temperature for 2 hours then washed in turn with water, 2M hydrochloric acid, water, 1M sodium carbonate and water. The organic solution was dried (magnesium sulphate) and evaporated under reduced pressure to give N-(3-trifluoromethylphenyl)-2-(6-difluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (compound 2, 0.25 g) as a beige solid, m.p. 58-60° C.

Workup

  1. temperaturecooled to 0° C
  2. stirringThe reaction mixture was stirred at 0° C. for 30 minutes and at ambient temperature for 2 hours
  3. washthen washed in turn with water, 2M hydrochloric acid, water, 1M sodium carbonate and water
  4. dry with materialThe organic solution was dried (magnesium sulphate)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ec2af2f79f0345198faab200efab0cb5
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

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