Water → HCID 178503981, compound

HRID 1870825Notes

Reaction equation

HRID 1870825 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([C:10]2[CH:14]=[C:13]([NH:15][C:16]([NH2:18])=[S:17])[O:12][N:11]=2)[CH3:9])[CH:5]=[CH:4][C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CI.[C:27](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([C:10]2[CH:14]=[C:13]([NH:15][C:16](=[NH:18])[S:17][CH3:27])[O:12][N:11]=2)[CH3:9])[CH:5]=[CH:4][C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15676038HCID 15676038, compound

Product 1

HCID 178503981HCID 178503981, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[1-(2-Fluoro-biphenyl-4-yl)-ethyl]-isoxazol-5-yl-thiourea (Japanese Patent Unexamined Publication No. 63-152368) (3.03 g) was dissolved in N,N-dimethylformamide (90 ml), followed by adding thereto methyl iodide (1.51 g) and potassium carbonate (0.86 g), and the resulting mixture was stirred at 40° C. for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate, and the extract solution was washed with water and dried. The solvent was distilled off under reduced pressure and the residue was purified by a silica gel column chromatography to obtain the desired compound (2.67 g).

Workup

  1. additionby adding
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe extract solution was washed with water
  4. customdried
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-f929b0cf02a147fca52aff88b1956ef6
Source dataset
uspto-grants-2000_08
Patent number
US06100260

Reaction notes

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