Triethylamine → HCID 54422257, compound

HRID 1740129Notes

Reaction equation

HRID 1740129 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH:11]([N:14]=[C:15]=[O:16])([CH3:13])[CH3:12].C(N(CC)CC)C>C1C=CC=CC=1>[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][O:1][C:15](=[O:16])[NH:14][CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 54422257HCID 54422257, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of α-hydroxyacetophenone (7.0 g, 51.4 mmol), isopropyl isocyanate (10.1 ml, 102.8 mmol) and triethylamine (7.2 ml, 51.4 mmol) in 150 ml of benzene was refluxed under nitrogen overnight. The reaction was diluted with benzene, extracted with 1N HCl, dried (MgSO4) and the solvent removed under reduced pressure to 9.741 g of a brown solid. Recrystallization of the solid from isopropyl alcohol gave isopropyl-carbamic acid 2-oxo-2-phenyl-ethyl ester (4.2 g, 38%) as yellow solid, mp 108-110° C.

Workup

  1. temperaturewas refluxed under nitrogen overnight
  2. extractionextracted with 1N HCl
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under reduced pressure to 9.741 g of a brown solid
  5. customRecrystallization of the solid from isopropyl alcohol

Sources & evidence

ORD record
ord-cf0dbed42c524fc6a4d1f9dbffdac576
Source dataset
uspto-grants-1999_10
Patent number
US05968975

Reaction notes

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