Chlorosuccinimide → [4-chloro-2-(1-methylethyl)-1H-imidazol-5-yl]methanol

HRID 439602Notes

Reaction equation

HRID 439602 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH:9]([C:12]1[NH:13][C:14]([CH2:19][OH:20])=[C:15](CO)[N:16]=1)([CH3:11])[CH3:10]>C(O)C>[CH:9]([C:12]1[NH:13][C:14]([CH2:19][OH:20])=[C:15]([Cl:1])[N:16]=1)([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 136089212-Isopropyl-4,5-bis(hydroxymethyl) imidazole

Product 1

HCID 15338147[4-chloro-2-(1-methylethyl)-1H-imidazol-5-yl]methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.81 Grams (21 mmol) of the N-chlorosuccinimide was added little by little to a solution consisting of 3.47 g (20.4 mmol) of a 2-isopropyl-4,5-bis(hydroxymethyl) imidazole and 220 ml of ethanol at a temperature of 40° to 45° C. with stirring over a period of about 25 minutes. The mixture was stirred at the same temperature for two hours to effect the reaction, and then ethanol was distilled off under reduced pressure. The resulting reaction product was washed with water to obtain a pale yellowish powdery crystalline 2-isopropyl-4-chloro-5-(hydroxymethyl) imidazole in an amount of 1.69 g (yield, 47.4%). By using acetonitrile, the recrystallization was effected twice to obtain a colorless crystalline product in pure form. The TLC and spectra of this compound were the same as the properties exhibited by the above-mentioned 2-isopropyl-4-chloro-5-(hydroxymethyl) imidazole.

Workup

  1. stirringThe mixture was stirred at the same temperature for two hours
  2. customthe reaction
  3. distillationethanol was distilled off under reduced pressure
  4. customThe resulting reaction product
  5. washwas washed with water

Sources & evidence

ORD record
ord-46a536f99f7542169b148789ff81435f
Source dataset
uspto-grants-1996_05
Patent number
US05514811

Reaction notes

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