N,N-Dimethylaniline → HCID 19105282, compound

HRID 1197891Notes

Reaction equation

HRID 1197891 reaction equation
[NH2:1][C:2]1[C:3](=[O:21])[O:4][C:5]2[CH:18]=[C:17]([CH3:19])[C:16]([Cl:20])=[CH:15][C:6]=2[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14].CN(C)C1C=CC=CC=1.[F:31][C:32]1[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:33]=1[C:34](Cl)=[O:35]>ClCCl>[Cl:20][C:16]1[C:17]([CH3:19])=[CH:18][C:5]2[O:4][C:3](=[O:21])[C:2]([NH:1][C:34](=[O:35])[C:33]3[CH:37]=[CH:38][C:39]([F:41])=[CH:40][C:32]=3[F:31])=[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH3:14])[C:6]=2[CH:15]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 5880812,4-Difluorobenzoyl chlorideHCID 10266781HCID 10266781, compound

Product 1

HCID 19105282HCID 19105282, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-amino-6-chloro-7-methyl-4-(2-methylphenyl)-2H-1-benzopyran-2- one (300 mg), N,N-dimethylaniline (0.13 ml) and dichloromethane (4 ml) was dropwise added 2,4-difluorobenzoyl chloride (0.15 ml). The mixture was stirred for 20 hours at room temperature, washed with water and dried (MgSO4). By distilling off the solvent, 6-chloro-3-(2,4-difluorobenzoylamino)-7-methyl-4-(2-methylphenyl)-2H-1-benzopyran-2-one was obtained as crystals (406 mg, 92.5%). Recrystallization from ethanol gave colorless prisms.

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. distillationBy distilling off the solvent

Sources & evidence

ORD record
ord-fd8abada297d467d8c5d8a2f74194fd5
Source dataset
uspto-grants-1994_01
Patent number
US05278186

Reaction notes

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