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

Participants

Role	Name	HCID	Charge
Reactant	4-Toluenesulfonyl chloride	HCID 7397	—
Reactant	N,N-Bis(2-hydroxyethyl)-4-methylbenzenesulfonamide	HCID 81565	—
Solvent	Pyridine	HCID 1049	—
Product	N,N-bis(2-(p-toluenesulfonyloxy)ethyl)-p-toluenesulfonamide	HCID 267409	—

Reaction Steps

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°].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04001279
Source dataset	uspto-grants-1977_01
ORD ID	ord-0ab10b2563654590921d806eedcd1473
Source note	uspto-grants-1977_01