Thionyl Chloride → 4-((5-(Chloromethyl)-1H-imidazol-1-yl)methyl)benzonitrile hydrochloride

HRID 1601037Notes

Reaction equation

HRID 1601037 reaction equation
[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH2:13]O)=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].S(Cl)([Cl:19])=O>>[ClH:19].[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH2:13][Cl:19])=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 101982471-(4-Cyanobenzyl)-5-hydroxymethyl-1H-imidazole

Product 1

HCID 97953574-((5-(Chloromethyl)-1H-imidazol-1-yl)methyl)benzonitrile hydrochloride

Conditions

Temperature
60 °C

Procedure

A suspension of 1-(4-cyanobenzyl)-5-(hydroxymethyl)-imidazole from Example 1, Step 4 (3.1 g) in thionyl chloride (20 mL) was heated at 60° C. for 16 h. The reaction was concentrated in vacuo, azeotroped with CHCl3 and filtered to give the title compound as a pale yellow solid which was sufficiently pure for use in the next step without further purification.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customazeotroped with CHCl3
  3. filtrationfiltered

Sources & evidence

ORD record
ord-75f4d744450d44eab215987e5f2dbf55
Source dataset
uspto-grants-1999_11
Patent number
US05977134

Reaction notes

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