Tert-Butylamine → N-(tert-Butyl)-3-iodobenzenesulfonamide

HRID 1825310Notes

Reaction equation

HRID 1825310 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[I:6][C:7]1[CH:8]=[C:9]([S:13](Cl)(=[O:15])=[O:14])[CH:10]=[CH:11][CH:12]=1.C(N(CC)CC)C>ClCCl>[C:1]([NH:5][S:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([I:6])[CH:8]=1)(=[O:15])=[O:14])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 39766m-Iodobenzenesulphonyl chloride

Product 1

HCID 11450619N-(tert-Butyl)-3-iodobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butylamine (300 mg) was added to a stirred, cooled (ice-bath) solution of 3-iodobenzenesulfonyl chloride (Bromidge et al, J. Med. Chem., 1999, 42(2), 202-205) and triethylamine (420 mg) in dichloromethane (7 ml). The mixture was then stirred for 2 h at room temperature, diluted with dichloromethane (10 ml) and washed with 2M hydrochloric acid (5 ml). The mixture was separated on a hydrophobic frit and the organic phase was evaporated to give the title compound (1.26 g). LCMS ES+ve 340 (MH)+.

Workup

  1. washwashed with 2M hydrochloric acid (5 ml)
  2. customThe mixture was separated on a hydrophobic frit
  3. customthe organic phase was evaporated

Sources & evidence

ORD record
ord-b45913e31310471398ac352c7c7ec5c0
Source dataset
uspto-grants-2006_05
Patent number
US07045658B2

Reaction notes

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