Tert-Butylamine → N-tert-butyl-1-phenylmethanesulfonamide

HRID 1505618Notes

Reaction equation

HRID 1505618 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[C:15]1([CH2:21][S:22](Cl)(=[O:24])=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClCCl>[C:1]([NH:5][S:22]([CH2:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:24])=[O:23])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 74740Phenylmethanesulfonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 562762N-tert-butyl-1-phenylmethanesulfonamideYield 77.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butylamine (2 g, 27.3 mmol) in dichloromethane (90 mL) was added N,N-diisopropylethylamine (5.7 mL, 32.8 mmol), followed by phenylmethanesulfonyl chloride (6.25 g, 32.8 mmol) and the reaction was stirred at ambient temperature for 16 hours. The reaction was then diluted with dichloromethane, washed with water and brine, dried with MgSO4, and purified by silica gel column chromatography (0-50% EtOAc in heptane) to give N-tert-butyl-1-phenyl-methanesulfonamide (4.81 g, 77% yield). 1H NMR (400 MHz, CDCl3) δ 7.51-7.44 (m, 2H), 7.41 (dd, J=4.9, 2.0 Hz, 3H), 4.49 (s, 2H), 4.27 (s, 1H), 1.68 (s, 6H); LCMS (m/z) ES+ 228 [M+1]+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried with MgSO4
  3. custompurified by silica gel column chromatography (0-50% EtOAc in heptane)

Sources & evidence

ORD record
ord-4aefc21189324d83b9bf1c3c3c5afdee
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

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