Chlorosuccinimide → 2-Butyl-4-chloro-5-(hydroxymethyl)imidazole

HRID 2399244Notes

Reaction equation

HRID 2399244 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([CH2:10][OH:11])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[Cl:12]N1C(=O)CCC1=O>O1CCCC1.COCC>[CH2:1]([C:5]1[NH:6][C:7]([CH2:10][OH:11])=[C:8]([Cl:12])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 27356732-Butyl-5-hydroxymethylimidazole

Product 1

HCID 27356622-Butyl-4-chloro-5-(hydroxymethyl)imidazoleYield 52.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 10903MethoxyethaneSolvent

Procedure

To a solution of 2-n-butyl-5-hydroxymethylimidazole (25 g, 0.162 mol, prepared in Example 1 (i)) in 250 ml of tetrahydrofuran and 250 ml of 2-methoxyethane under argon was added portionwise N-chlorosuccinimide (26 g, 0.195 mol). The reaction mixture was heated at 50°-55° C. for 2 hours. The solvents were removed in vacuo and the residue for 48 hours. The solid was filtered and then stirred with 100 ml of diethyl ether for 1 hour. The solid was collected to give 16 g (52%) of 2-n-butyl-4-chloro-5-hydroxymethylimidazole.

Workup

  1. temperatureThe reaction mixture was heated at 50°-55° C. for 2 hours
  2. customThe solvents were removed in vacuo
  3. filtrationThe solid was filtered
  4. customThe solid was collected

Sources & evidence

ORD record
ord-24ec1990e46f479d93723cd5a24c2c4e
Source dataset
uspto-grants-1995_09
Patent number
US05447949

Reaction notes

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