Water → N-(4-Bromophenyl)methanesulfinamide

HRID 1485606Notes

Reaction equation

HRID 1485606 reaction equation
[CH3:1][S:2](Cl)=[O:3].[Br:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1.C(N(CC)C(C)C)(C)C.O>ClCCl>[Br:5][C:6]1[CH:12]=[CH:11][C:9]([NH:10][S:2]([CH3:1])=[O:3])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78074-BromoanilineHCID 81531DiisopropylethylamineHCID 548463Methanesulfinyl chloride

Product 1

HCID 14195208N-(4-Bromophenyl)methanesulfinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulfinyl chloride (2.06 g) in dichloromethane (20 mL) is added drop wise to an ice-cooled mixture of 4-bromoaniline (3.00 g) and N,N-diisopropylethylamine (10.63 mL) in dichloromethane (20 mL). The reaction mixture is allowed to warm to room temperature and stirred for 5 h. Water is added to the mixture and the organic phase is separated, washed with water, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 50:500:100) to give the title compound. LC (method 1): tR=0.82 min; Mass spectrum (ESI+): m/z=234, 236 [M+H]+.

Workup

  1. temperaturecooled
  2. customthe organic phase is separated
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 50:500:100)

Sources & evidence

ORD record
ord-a794706757b84302b794ff1f2eb4f32d
Source dataset
uspto-grants-2016_08
Patent number
US09422312B2

Reaction notes

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