Tert-Butylamine → N-(tert-butyl)-2-methoxybenzenesulfonamide

HRID 2264124Notes

Reaction equation

HRID 2264124 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9](Cl)(=[O:11])=[O:10].[C:13]([NH2:17])([CH3:16])([CH3:15])[CH3:14]>ClCCl>[C:13]([NH:17][S:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])(=[O:11])=[O:10])([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 37458512-Methoxybenzenesulfonyl Chloride

Product 1

HCID 23448664N-(tert-butyl)-2-methoxybenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 30.00 g (145.17 mmol) of 2-methoxybenzenesulfonyl chloride in 150 ml of dichloromethane is admixed dropwise at 5-10° C. with 22.30 g (304.87 mmol) of tert-butylamine. The mixture is then stirred at room temperature for 2 h. Following extraction with water, the organic phase is dried over sodium sulfate and evaporated to dryness. This gives 31.10 g (88% of theory) of N-(tert-butyl)-2-methoxybenzenesulfonamide.

Workup

  1. extractionextraction with water
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-46014a01d81e47f3aa6d177af405abde
Source dataset
uspto-grants-2010_12
Patent number
US07855166B2

Reaction notes

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