Dimethylamine → 5-Chloro-N,N-dimethyl-2-nitro-benzenesulfonamide

HRID 1041122Notes

Reaction equation

HRID 1041122 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:7]=1.[CH3:15][NH:16][CH3:17]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([S:8]([N:16]([CH3:17])[CH3:15])(=[O:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 116732955-Chloro-2-nitrobenzene-1-sulfonyl chloride

Product 1

HCID 672642335-Chloro-N,N-dimethyl-2-nitro-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-Chloro-2-nitro-benzenesulfonyl chloride (2.0 g, 0.0078 mol) (Lebegue, N.; Gallet, S.; Flouquet, N.; Carato, P.; Pfeiffer, B.; Renard, P.; Leonce, S.; Pierre, A.; Chavatte, P.; Berthelot, P. J. Med. Chem. (2005), 48(23), 7363-7373) in Tetrahydrofuran (10 mL, 0.1 mol) was added 2.0 M of Dimethylamine in Tetrahydrofuran (7.8 mL). The mixture was stirred for 18 hours. The mixture was evaporated and water was added then agitated until a solid precipitated. The solid was filtered and dried. 5-Chloro-N,N-dimethyl-2-nitro-benzenesulfonamide isolated as yellow solid (1.87 g, 90%).

Workup

  1. customThe mixture was evaporated
  2. additionwater was added
  3. stirringthen agitated until a solid
  4. customprecipitated
  5. filtrationThe solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-6d64b1e7761f427d83691820e0f0f39a
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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