Ethyl isocyanate → HCID 59577314, compound

HRID 2041986Notes

Reaction equation

HRID 2041986 reaction equation
[C:1]([C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH:8]1[CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH2:16]([N:18]=[C:19]=[O:20])[CH3:17]>N1C=CC=CC=1>[C:1]([C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH:8]1[CH2:9][N:10]([C:19]([NH:18][CH2:16][CH3:17])=[O:20])[CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 534095303-(2-Tert-butylphenoxy)azetidine

Product 1

HCID 59577314HCID 59577314, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 3-(2-tert-Butylphenoxy)azetidine (0.21 g, 1.02 mmol) in pyridine (10 ml) was added ethyl isocyanate (0.078 g, 1.10 mmol) and the mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was washed with water and saturated sodium chloride, dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was triturated with heptane/ethyl acetate to provide 3-(2-tert-Butylphenoxy)-N-ethylazetidine-1-carboxamide (0.15 g, 53%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was partitioned between ethyl acetate and 1N hydrochloric acid
  3. washThe organic layer was washed with water and saturated sodium chloride
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was triturated with heptane/ethyl acetate

Sources & evidence

ORD record
ord-c83e5fb0c7544e12acc598e28a15097b
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

Loading…