Isopropanol → HCID 178459416, compound

HRID 2089463Notes

Reaction equation

HRID 2089463 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=[O:7])[N:3]=[CH:2]1.S(Cl)(Cl)=O.[CH3:13][CH:14](O)[CH3:15]>>[CH:14]([O:7][C:6]([C:4]1[N:3]=[CH:2][NH:1][CH:5]=1)=[O:8])([CH3:15])[CH3:13]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 24386Thionyl ChlorideHCID 178524800HCID 178524800, compound

Product 1

HCID 178459416HCID 178459416, compound

Procedure

To imidazole-4-carboxylic acid (CAS#1072-84-0, 3.0 g, 26.7 mmol) in propan-2-ol (60 mL) is added thionyl chloride (15.9 g, 13.4 mmol) and the solution is refluxed overnight. The volatiles are removed in vacuo and the residue is partitioned between ethyl acetate and 4M aqueous sodium hydroxide. The organic layer is dried-over Na2SO4, filtered and concentrated to afford imidazole-4-carboxylic acid isopropyl ester; MS: (ESI) m/z 155.0 (M+H)+.

Workup

  1. temperaturethe solution is refluxed overnight
  2. customThe volatiles are removed in vacuo
  3. customthe residue is partitioned between ethyl acetate and 4M aqueous sodium hydroxide
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a4dbb544f3634931bea059916fa43fcd
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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