Dimethylamine → N'-(4-Bromophenyl)-N,N-dimethyl-methanesulfonimidamide

HRID 1485607Notes

Reaction equation

HRID 1485607 reaction equation
CC([O-])(C)C.[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:17])=[O:16])=[CH:10][CH:9]=1.Cl[N:19]1[C:23](=O)CC[C:20]1=O.CNC>C(#N)C>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]=[S:15]([CH3:17])([N:19]([CH3:23])[CH3:20])=[O:16])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 31398ChlorosuccinimideHCID 14195208N-(4-Bromophenyl)methanesulfinamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 118863925N'-(4-Bromophenyl)-N,N-dimethyl-methanesulfonimidamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium tert-butylate (958 mg) is added to a mixture of N-(4-bromophenyl)methanesulfinamide (1.00 g), N-chlorosuccinimide (684 mg), and dimethylamine solution (2 M in tetrahydrofuran; 6.41 mL) in acetonitrile at room temperature under an argon atmosphere. The reaction mixture is stirred at room temperature for 2 days. The reaction mixture is partitioned between water and ethyl acetate and the aqueous phase is extracted with ethyl acetate. The combined extracts are washed with brine, 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=0.95 min; Mass spectrum (ESI+): m/z=277, 279 [M+H]+.

Workup

  1. customThe reaction mixture is partitioned between water and ethyl acetate
  2. extractionthe aqueous phase is extracted with ethyl acetate
  3. washThe combined extracts are washed with brine
  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-737bb9aa3ffd432f8a279509915dd8a7
Source dataset
uspto-grants-2016_08
Patent number
US09422312B2

Reaction notes

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