4-Toluenesulfonyl chloride → N,N-bis(2-(p-toluenesulfonyloxy)ethyl)-p-toluenesulfonamide

HRID 1414445

Reaction equation

HRID 1414445 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:15][CH2:16][OH:17])[S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>N1C=CC=CC=1>[S:5]([N:4]([CH2:15][CH2:16][O:17][S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH2:3][CH2:2][O:1][S:18]([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19])([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 81565N,N-Bis(2-hydroxyethyl)-4-methylbenzenesulfonamide

Product 1

HCID 267409N,N-bis(2-(p-toluenesulfonyloxy)ethyl)-p-toluenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Procedure 3 is illustrated with the preparation of (-)-(RR)-8a' and (+)-(RR)-8b', with (-)-(R)-6f' as a byproduct. In dry pyridine at 0°, N,N-bis-(2-hydroxyethyl)-p-toluenesulfonamide (m.p. 96°-99°) was tosylated with tosyl chloride by the standard method to give N,O,O'-tritosyldiethanolamine, m.p. 85°-87°. [Can. J. Chem. 45, 1555 (1967) gives 78°-79°].

Workup

  1. customProcedure 3 is illustrated with the preparation of (-)-(RR)-8a' and (+)-(RR)-8b', with (-)-(R)-6f' as a byproduct
  2. customat 0°

Sources & evidence

ORD record
ord-0ab10b2563654590921d806eedcd1473
Source dataset
uspto-grants-1977_01
Patent number
US04001279

Linked notes

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