Methylamine → N-Methyl-4-nitrobenzenesulfonamide

HRID 57230Notes

Reaction equation

HRID 57230 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:14]([N:16](CC)CC)C.CN>C1COCC1.[Cl-].[Na+].O>[CH3:14][NH:16][S:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:12])=[O:11]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 232993N-Methyl-4-nitrobenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To an ice cold solution of 4-nitrobenzenesulfonyl chloride (2.7 g, 12 mmol) and triethylamine (27 mmol) in 60 mL of dry THF was added methylamine (8 mL of a 2 M solution in THF, 16 mmol). The mixture was stirred at room temperature overnight. Brine was added and the reaction solution was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and evaporated to yield 4-nitrobenzenesulfonic acid methylamide as an oil. The crude material was used in the subsequent reaction without further purification.

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-a67356e0507b4344a8b72abc7c120994
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Reaction notes

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