Dimethylamine → N,N,2-trimethyl-5-nitro-Benzenesulfonamide

HRID 1167240Notes

Reaction equation

HRID 1167240 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11](Cl)(=[O:13])=[O:12].[CH3:15][NH:16][CH3:17]>CO.O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([N:16]([CH3:17])[CH3:15])(=[O:13])=[O:12]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 8457o-Toluenesulfonyl chloride, 5-nitro-

Product 1

HCID 2921148N,N,2-trimethyl-5-nitro-BenzenesulfonamideYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-methyl-5-nitrobenzenesulfonyl chloride (5.0 g, 21.2 mmol) in 100 mL of methanol at 0° C. was added dimethylamine (5.3 mL of a 40% aqueous solution). The resulting reaction mixture was stirred at 0° C. for 10 min, during which time the product crashed out as white needles. The mixture was diluted with water and filtered, washing once with water. The needles were collected and dried in vacuo to provide 2-methyl-5-nitro(N,N-dimethyl)benzenesulfonamide (4.4 g, 85%), mp 72-74° C.

Workup

  1. customThe resulting reaction mixture
  2. filtrationfiltered
  3. washwashing once with water
  4. customThe needles were collected
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ccf2205cada4479ea9390f52bd9b2e83
Source dataset
uspto-grants-2003_09
Patent number
US06617357B2

Reaction notes

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