Thionyl Chloride → HCID 15616313, compound

HRID 2379134Notes

Reaction equation

HRID 2379134 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[N:8]=[CH:9][N:10]([S:15]([N:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[C:11]=1[CH2:12][CH2:13][CH3:14]>ClCCl>[Cl:3][CH2:6][C:7]1[N:8]=[CH:9][N:10]([S:15]([N:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[C:11]=1[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15616312HCID 15616312, compound

Product 1

HCID 15616313HCID 15616313, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of thionyl chloride (0.12 ml) in dry dichloromethane (1.2 ml) was added dropwise to a cold (0°) stirred solution of 4-(hydroxymethyl)-N,N-dimethyl-5-propyl-1H-imidazole-1-sulphonamide (340 mg) in dry dichloromethane (7.5 ml) under nitrogen. After 1.5 h the solution was washed with 8% sodium bicarbonate solution (2×15 ml) and the aqueous phase was extracted with dichloromethane (2×10 ml). The combined organic extracts were washed with water (15 ml), dried and evaporated to give the title compound (180 ml) as an oil, t.l.c. (ethyl acetate) Rf 0.68.

Workup

  1. washAfter 1.5 h the solution was washed with 8% sodium bicarbonate solution (2×15 ml)
  2. extractionthe aqueous phase was extracted with dichloromethane (2×10 ml)
  3. washThe combined organic extracts were washed with water (15 ml)
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-ee71b7c70a1c4d69849cdc9c90b559fd
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

Loading…