Thionyl Chloride → HCID 21421761, compound

HRID 259427Notes

Reaction equation

HRID 259427 reaction equation
[C:1]1([CH:7]([N:9]2[C:13]([C:14]([OH:16])=O)=[CH:12][N:11]=[CH:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:19])=O>>[ClH:19].[C:1]1([CH:7]([N:9]2[C:13]([C:14]([Cl:19])=[O:16])=[CH:12][N:11]=[CH:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 297427Desethyl-etomidate

Product 1

HCID 21421761HCID 21421761, compoundYield 94%

Procedure

A mixture of 25.5 parts of (-)-1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid and 280 parts of sulfinyl chloride is stirred and refluxed for 2 hours. The reaction mixture is cooled in an ice-bath. The product crystallizes upon the addtion of 2,2'-oxybispropane. It is filtered off, washed with 2,2'-oxybispropane and dried, yielding 94% of (-)-1-(1-phenylethyl)-1H-imidazole-5-carbonyl chloride hydrochloride.

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureThe reaction mixture is cooled in an ice-bath
  3. customThe product crystallizes upon the addtion of 2,2'-oxybispropane
  4. filtrationIt is filtered off
  5. washwashed with 2,2'-oxybispropane
  6. customdried

Sources & evidence

ORD record
ord-df2c3172bd7548a9a230ee5fd86621c1
Source dataset
uspto-grants-1977_07
Patent number
US04038286

Reaction notes

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