Thionyl Chloride → HCID 18670818, compound

HRID 1638262Notes

Reaction equation

HRID 1638262 reaction equation
[ClH:1].[C:2]1([CH:8]([N:10]2[C:14]([CH2:15]O)=[CH:13][N:12]=[CH:11]2)[CH3:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O>CC(O)C>[ClH:19].[Cl:1][CH2:15][C:14]1[N:10]([CH:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH3:9])[CH:11]=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20068385HCID 20068385, compound

Product 1

HCID 18670818HCID 18670818, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3 Parts of 1-(1-phenylethyl)-1H-imidazole-5-methanol monohydrochloride were added portionwise to 16 parts of thionyl chloride (exothermic reaction with evolution of SO2 /HCl). After the addition was complete, the whole was stirred and refluxed for 30 minutes. After cooling there were added 40 parts of 2-propanol, whereupon a solid was precipitated. It was filtered off and recrystallized from a mixture of 60 parts of 2-propanol and 60 parts of 2,2'-oxybispropane, yielding 1.5 parts of 5-(chloromethyl)-1-(1-phenylethyl)-1H-imidazole monohydrochloride; mp. 173.5-175° C. (dec.) (compound 8.49).

Workup

  1. additionAfter the addition
  2. temperaturerefluxed for 30 minutes
  3. temperatureAfter cooling there
  4. customwhereupon a solid was precipitated
  5. filtrationIt was filtered off
  6. customrecrystallized from a mixture of 60 parts of 2-propanol and 60 parts of 2,2'-oxybispropane

Sources & evidence

ORD record
ord-a8c5664028a847f1bd1d6d4de17d8c7f
Source dataset
uspto-grants-1989_11
Patent number
US04878940

Reaction notes

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