Chlorosuccinimide → HCID 13074115, compound

HRID 223514Notes

Reaction equation

HRID 223514 reaction equation
[CH2:1]([N:8]1[C:12]([CH2:13][C:14]#[N:15])=[C:11]([Cl:16])[N:10]=[C:9]1[C:17]1[CH:22]=[CH:21][C:20]([N:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:26]N1C(=O)CCC1=O>O1CCOCC1>[CH2:1]([N:8]1[C:12]([CH2:13][C:14]#[N:15])=[C:11]([Cl:16])[N:10]=[C:9]1[C:17]1[CH:22]=[CH:21][C:20]([N:23]([CH3:24])[CH3:25])=[C:19]([Cl:26])[CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 13022619HCID 13022619, compound

Product 1

HCID 13074115HCID 13074115, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2 g of 1-benzyl-4-chloro-5-cyanomethyl-2-(4-dimethylaminophenyl)imidazole and 1 g of N-chlorosuccinimide were stirred in 30 ml of dioxane at 50° C. for 2 hours. The reaction solution was evaporated to dryness under reduced pressure, and the residue was dissolved in 100 ml of chloroform, followed by washing twice with water and evaporating to dryness under reduced pressure. The residue was recrystallized twice from 20 ml of methanol, thus yielding 1.4 g of 1-benzyl-4-chloro-5-cyanomethyl-2-(4-dimethylamino-3-chlorophenyl)imidazole as slightly yellow, needle-formed crystals, m.p. 142°-143° C.

Workup

  1. customThe reaction solution was evaporated to dryness under reduced pressure
  2. dissolutionthe residue was dissolved in 100 ml of chloroform
  3. washby washing twice with water
  4. customevaporating to dryness under reduced pressure
  5. customThe residue was recrystallized twice from 20 ml of methanol

Sources & evidence

ORD record
ord-117fa9a99ee049739e78968c9166b012
Source dataset
uspto-grants-1982_10
Patent number
US04355040

Reaction notes

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