Ethanolamine → N-(2-hydroxyethyl)-2,4-dimethylbenzenesulfonamide

HRID 1834345Notes

Reaction equation

HRID 1834345 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].C(N(CC)CC)C.[CH3:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=1[S:20](Cl)(=[O:22])=[O:21]>O1CCCC1>[OH:2][CH2:1][CH2:3][NH:4][S:20]([C:14]1[CH:15]=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=1[CH3:12])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 69109Benzenesulfonyl chloride, 2,4-dimethyl-

Product 1

HCID 15942937N-(2-hydroxyethyl)-2,4-dimethylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 40 parts of tetrahydrofuran are added 1.5 parts of ethanolamine and 2.5 parts of triethylamine. Into this solution, 10 parts of tetrahydrofuran containing 5 parts of 2,4-dimethylbenzenesulfonyl chloride is dropped with stirring. After the dropping, the resultant mixture is stirred as it is for 30 minutes. Subsequently, the salt is removed by filtration, and the filtrate is freed from the solvent to form a solid. This solid is recrystallized from isopropyl ether to obtain 3.6 parts of N-2-hydroxyethyl-2,4-dimethylbenzenesulfonamide, m.p. 70°-72° C.

Workup

  1. customSubsequently, the salt is removed by filtration
  2. customto form a solid
  3. customThis solid is recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-20408ad42c75413db49e303829290e68
Source dataset
uspto-grants-1978_01
Patent number
US04070176

Reaction notes

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