Benzyl Chloride → HCID 10094402, compound

HRID 1087228Notes

Reaction equation

HRID 1087228 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[C:10]([C:12]1[CH:22]=[CH:21][C:15]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[C:14]([S:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[F:31])[CH:13]=1)#N.[Cl-].[NH4+].[O:34]1CCCC1>O.C(OCC)(=O)C>[F:31][C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[S:23][C:14]1[CH:13]=[C:12]([C:10](=[O:34])[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:22]=[CH:21][C:15]=1[NH:16][S:17]([CH3:20])(=[O:19])=[O:18]

Participants

8

Reactant 5

HCID 7503Benzyl ChlorideHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 10404983HCID 10404983, compound

Product 1

HCID 10094402HCID 10094402, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl chloride (1.92 ml) was added dropwise to a mixture of magnesium (357 mg) in tetrahydrofuran (15 ml) at 40° C. The mixture was stirred at room temperature for 40 minutes. To the resulting solution was added a solution of 4'-cyano-2'-(2,4-difluorophenylthio)methanesulfonanilide (1 g) in tetrahydrofuran (15 ml) dropwise at room temperature. The reaction mixture was stirred for 1 hour and hydrolyzed with cold ammonium chloride solution. Ethyl acetate (30 ml) and water (30 ml) were added. The organic layer was separated, shaken with diluted hydrochloric acid, dried, and evaporated. The residual oil (2.2 g) was purified by column chromatography on silica gel (40 g) eluting with a mixture of toluene and ethyl acetate (40:1) followed by recrystallization from ethanol to give pale brown crystals of 2'-(2,4-difluorophenylthio)-4'-(phenylacetyl)methanesulfonanilide (0.52 g).

Workup

  1. customThe organic layer was separated
  2. stirringshaken with diluted hydrochloric acid
  3. customdried
  4. customevaporated
  5. customThe residual oil (2.2 g) was purified by column chromatography on silica gel (40 g)
  6. washeluting with a mixture of toluene and ethyl acetate (40:1)
  7. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-a128fa9ac5ca4eb982a02141d9f61011
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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