Ethanolamine → N-(2-Hydroxyethyl)-2-[N-(2-hydroxyethyl)aminosulfonyl]-6-nitrobenzamide

HRID 231576Notes

Reaction equation

HRID 231576 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2[C:10]([N+:14]([O-:16])=[O:15])=[CH:11][CH:12]=[CH:13][C:6]=2[S:5]1(=[O:18])=[O:17].[CH2:19]([CH2:21][NH2:22])[OH:20]>C1COCC1>[OH:20][CH2:19][CH2:21][NH:22][C:8](=[O:9])[C:7]1[C:10]([N+:14]([O-:16])=[O:15])=[CH:11][CH:12]=[CH:13][C:6]=1[S:5]([NH:4][CH2:3][CH2:2][OH:1])(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 138812912-(2-hydroxyethyl)-4-nitro-2H-1,2-benzisothiazol-3-one 1,1-dioxide

Product 1

HCID 13881296N-(2-Hydroxyethyl)-2-[N-(2-hydroxyethyl)aminosulfonyl]-6-nitrobenzamideYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(2-hydroxyethyl)-4-nitro-2H-1,2-benzisothiazol-3-one 1,1-dioxide (100 mg, 0.37 mmol) and ethanolamine (24 mg, 0.39 mmol) in THF (5 ml) was allowed to stand at 20-25° for 3 days. After removal of THF under reduced pressure, the residue was recrystallized from MeOH-EtOAc-hexane to give 112 mg (91%) of product, m.p. 176.5-177.5°.

Workup

  1. customAfter removal of THF under reduced pressure
  2. customthe residue was recrystallized from MeOH-EtOAc-hexane

Sources & evidence

ORD record
ord-674f9cadedeb4a02a3a39cf3c9a1377c
Source dataset
uspto-grants-1989_07
Patent number
US04847294

Reaction notes

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