Chlorosuccinimide → HCID 15338149, compound

HRID 439603Notes

Reaction equation

HRID 439603 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH2:9]([C:20]1[NH:21][C:22]([CH2:27][OH:28])=[C:23](CO)[N:24]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>C(O)C>[CH2:9]([C:20]1[NH:21][C:22]([CH2:27][OH:28])=[C:23]([Cl:1])[N:24]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 15338148HCID 15338148, compound

Product 1

HCID 15338149HCID 15338149, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.10 Grams (8.3 mmol) of the N-chlorosuccinimide was added little by little to a solution consisting of 2.15 g (7.6 mmol) of a 2-undecyl-4,5-bis(hydroxymethyl) imidazole and 200 ml of ethanol at a temperature of 40° to 45° C. over a period of about 23 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 and was then recrystallized from acetone to obtain a creamy-white fine crystalline 2-undecyl-4-chloro-5-(hydroxymethyl) imidazole in an amount of 1.16 g (yield, 53.1%). By using acetonitrile, furthermore, 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 the above-mentioned 2-undecyl-4-chloro-5-(hydroxymethyl) imidazole.

Workup

  1. customthe reaction
  2. distillationethanol was distilled off under reduced pressure
  3. customThe resulting reaction product
  4. washwas washed with water
  5. customwas then recrystallized from acetone

Sources & evidence

ORD record
ord-7038f4d63a0f47038916a461c113741f
Source dataset
uspto-grants-1996_05
Patent number
US05514811

Reaction notes

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