Dimethylamine → HCID 11391437, compound

HRID 1991192Notes

Reaction equation

HRID 1991192 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[S:11](Cl)(=[O:13])=[O:12].[CH3:15][NH:16][CH3:17].C(N(CC)CC)C>CO>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[S:11]([N:16]([CH3:17])[CH3:15])(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8471TriethylamineHCID 230424882-chloro-3-nitrobenzene-1-sulfonyl chloride

Product 1

HCID 11391437HCID 11391437, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-Chloro-3-nitrobenzenesulfonyl chloride (235 mg, 0.918 mmol) was treated with a 2 M solution of dimethylamine in methanol (0.55 mL, 1.10 mmol), and triethylamine (0.13 mL, 0.918 mmol) in methanol (1 mL), and the suspension was stirred at room temperature for 2.5 h. The volatiles were removed in vacuo, and the residue was purified by column chromatography using heptane/ethyl acetate, 70:30-50:50 as an eluent, affording 2-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide, 202 mg (83%) as a white solid. MS (ESI) m/z 265 [M+H]. 1H NMR (400 MHz, CDCl3) δ ppm 2.95 (s, 6 H); 7.56 (t, J=8.0 Hz, 1H), 7.88 (dd, J=8.1, 1.5 Hz, 1H), 8.31 (dd, J=8.1, 1.5 Hz, 1H).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5927497239ed4c45af1671aeb12f3aee
Source dataset
uspto-grants-2010_01
Patent number
US07645784B2

Reaction notes

Loading…