Potassium Hydroxide → HCID 178418251, compound

HRID 2226893Notes

Reaction equation

HRID 2226893 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 4× with 500 ml of CH2Cl2 each time the combined organic extracts are washed 3× 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 4× with 500 ml of CH2Cl2 each time the combined organic extracts
  4. washare washed 3× with 300 ml of saturated aqueous NaHCO3 solution each time
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-809a6e1568644e12a71dc5a4f63dff4d
Source dataset
uspto-grants-1994_09
Patent number
US05350751

Reaction notes

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