Tert-Butylamine → N-tert-butylmethanesulfonamide

HRID 72367Notes

Reaction equation

HRID 72367 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([NH2:10])([CH3:9])([CH3:8])[CH3:7]>ClCCl>[C:6]([NH:10][S:2]([CH3:1])(=[O:4])=[O:3])([CH3:9])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 4130162N-tert-butylmethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7.74 ml of methanesulfonyl chloride in 100 ml of dichloromethane were added dropwise, at a temperature of 0° C., 23.12 ml of tert-butylamine. On completion of addition, the precipitate was filtered off and the filtrate was washed with 100 ml of 1 N aqueous hydrochloric acid, the organic phase was dried over MgSO4 and the solvent was removed under reduced pressure. The product (14.70 g) was obtained with a molecular weight of 151.2 g/mol (C5H13NO2S).

Workup

  1. additionOn completion of addition
  2. filtrationthe precipitate was filtered off
  3. washthe filtrate was washed with 100 ml of 1 N aqueous hydrochloric acid
  4. dry with materialthe organic phase was dried over MgSO4
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5a3bc98b320f4dada55ae9a70927a84e
Source dataset
uspto-grants-2014_09
Patent number
US08828994B2

Reaction notes

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