Hydrochloric Acid → 4-Methanesulphonamidophenethyl mesylate

HRID 2291568Notes

Reaction equation

HRID 2291568 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19].Cl>ClCCl>[CH3:17][S:18]([O:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:2]([NH:1][S:18]([CH3:17])(=[O:20])=[O:19])=[CH:3][CH:4]=1)(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 669044-Aminophenethyl alcohol

Product 1

HCID 149859624-Methanesulphonamidophenethyl mesylateYield 29.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Aminophenethyl alcohol (2.74 g) was dissolved in dichloromethane (10 ml) and pyridine (5 ml) and then methanesulphonyl chloride (2×2.52 g) was added in 2 portions one hour apart, with stirring at 0°. After a further 2 hours, the mixture was acidified (to pH about 2) with 2N aqueous hydrochloric acid. The title compound (4.85 g) was filtered from the two-phase mixture. The organic layer plus a further dichloromethane extract of the aqueous layer yielded a further 0.95 g product after drying (sodium sulphate) and evaporation. The combined solids were washed with ether and recrystallized from ethyl acetate, yield of the title compound 4.13 g, m.p. 135°-7°.

Workup

  1. filtrationThe title compound (4.85 g) was filtered from the two-phase mixture
  2. extractionThe organic layer plus a further dichloromethane extract of the aqueous layer

Sources & evidence

ORD record
ord-5178f98dfd884efcbf32f817002f519d
Source dataset
uspto-grants-1989_01
Patent number
US04797401

Reaction notes

Loading…