Potassium Hydroxide → HCID 178418251, compound

HRID 1756281Notes

Reaction equation

HRID 1756281 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([CH2:11][OH:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-].[K+]>O.C(O)(=O)C>[CH2:1]([C:5]1[NH:6][C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 27356622-Butyl-4-chloro-5-(hydroxymethyl)imidazole

Product 1

HCID 178418251HCID 178418251, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

305 ml of a 1M solution of (NH4)2Ce(NO3)6 in H2O are added slowly at 10°-15° C. to 20 g (0.106 mol) of 2-butyl-4-chloro-5-hydroxymethylimidazole in 350 ml of glacial acetic acid. After 2.5 h at RT, the pH is adjusted to 4 with 2N KOH (20° C. during addition of the base). After extraction 4x with 500 ml of CH2Cl2 each time the combined organic extracts are washed 3x with 300 ml of saturated aqueous NaHCO3 solution each time, dried with Na2SO4 and concentrated, resulting in the title compound as a colorless solid (18 g). Melting point was 90° C.

Workup

  1. custom20° C.
  2. additionduring addition of the base)
  3. extractionAfter extraction 4x with 500 ml of CH2Cl2 each time the combined organic extracts
  4. washare washed 3x with 300 ml of saturated aqueous NaHCO3 solution each time
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a18616d820e44c4db638cb4a9a1ccef0
Source dataset
uspto-grants-1995_08
Patent number
US05440046

Reaction notes

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