Thionyl Chloride → 1-Benzyl-4-chloro-5-(chloromethyl)-2(4-nitrophenyl)-imidazole

HRID 1385811Notes

Reaction equation

HRID 1385811 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([N:12]1[C:16]([CH2:17]O)=[C:15]([Cl:19])[N:14]=[C:13]1[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(Cl)(Cl)Cl>[CH2:5]([N:12]1[C:16]([CH2:17][Cl:3])=[C:15]([Cl:19])[N:14]=[C:13]1[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15088539(1-benzyl-4-chloro-2-(4-nitrophenyl)-1H-imidazol-5-yl)methanol

Product 1

HCID 223457251-Benzyl-4-chloro-5-(chloromethyl)-2(4-nitrophenyl)-imidazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thionyl chloride (0.90 ml, 1.48 g, 12.4 mmol) was added dropwise to a stirred suspension of 1-benzyl-4-chloro-5-(hydroxymethyl)-2(4-nitrophenyl)imidazole (18.5 g, 5.4 mmole) in chloroform (15 ml) at room temperature. The brown solution was stirred for 2.5 hours then evaporated to dryness. Toluene (12 ml) was added to the residue and evaporated to dryness. The residue was dissolved in chloroform (20 ml) and used in the next step for introduction of the cyano functional group.

Workup

  1. customthen evaporated to dryness
  2. additionToluene (12 ml) was added to the residue
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in chloroform (20 ml)

Sources & evidence

ORD record
ord-e65ce066a6564e1dbdaa13a395e04ea7
Source dataset
uspto-grants-2001_07
Patent number
US06264914B1

Reaction notes

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