m-Iodobenzenesulphonyl chloride → N2-[(3-Iodophenyl)sulfonyl]glycinamide

HRID 2118295Notes

Reaction equation

HRID 2118295 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.Cl.[NH2:13][CH2:14][C:15]([NH2:17])=[O:16].C(N(C(C)C)CC)(C)C>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]([S:8]([NH:13][CH2:14][C:15]([NH2:17])=[O:16])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 39766m-Iodobenzenesulphonyl chlorideHCID 81531DiisopropylethylamineHCID 2723639Glycinamide hydrochloride

Product 1

HCID 21895595N2-[(3-Iodophenyl)sulfonyl]glycinamideYield 42.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(3-Iodophenyl)sulphonyl chloride (0.303 g) was stirred with glycinamide hydrochloride (0.122 g) and diisopropylethylamine (0.3 ml) in DMF (4 ml) at 21° for 24 h. The mixture was evaporated to dryness and applied to a silica Bond Elut Cartridge (10 g). The cartridge was eluted with CH2Cl2, Et2O and EtOAc. This gave the title compound (0.146 g), LCMS RT=2.36 min, ES+ve 341 (MH)+

Workup

  1. customThe mixture was evaporated to dryness
  2. washThe cartridge was eluted with CH2Cl2, Et2O and EtOAc

Sources & evidence

ORD record
ord-3d776ae3a94347efacc0419670ba8534
Source dataset
uspto-grants-2008_10
Patent number
US07442837B2

Reaction notes

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