Isopropanol → Propan-2-yl (4-ethoxy-3-ethyl-5-methylphenyl)carbamate

HRID 2308733Notes

Reaction equation

HRID 2308733 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([CH3:13])[C:9]=1[O:10][CH2:11][CH3:12])[NH2:6])[CH3:2].[C:14](Cl)(Cl)=[O:15].[CH:18]([OH:21])([CH3:20])[CH3:19].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:4]=[C:5]([NH:6][C:14](=[O:15])[O:21][CH:18]([CH3:20])[CH3:19])[CH:7]=[C:8]([CH3:13])[C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 6371PhosgeneHCID 8471TriethylamineHCID 20187592HCID 20187592, compound

Product 1

HCID 13303943Propan-2-yl (4-ethoxy-3-ethyl-5-methylphenyl)carbamateYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 3-ethyl-4-ethoxy-5-methylaniline (1.8 g) in toluene (20 ml) was dropwise added to a toluene solution containing 10 g of phosgene at 10° to 20° C. The resulting mixture was gradually heated and, after being refluxed for 30 minutes, cooled to room temperature. The solvent was removed by distillation under reduced pressure to gove 3-ethyl-4-ethoxy-5-methylphenyl isocyanate (2.1 g). The thus obtained crude substance was added to an isopropanol solution (20 ml) containing triethylamine (1 g). The resultant mixture was allowed to stand at room temperature for 12 hours, poured into ice-water and extracted with toluene. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography using toluene as the eluent to give isopropyl N-(3-ethyl-4-ethoxy-5-methylphenyl)carbamate (Compound No. 93) (2.4 g) in a yield of 91% (calculated from the starting 3-ethyl-4-ethoxy-5-methylaniline). M.P., 68°- 69.5° C.

Workup

  1. temperatureThe resulting mixture was gradually heated
  2. temperatureafter being refluxed for 30 minutes
  3. customThe solvent was removed by distillation under reduced pressure
  4. customThe thus obtained crude substance
  5. extractionextracted with toluene
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-36cfb7257a1847f68f6afc25af8fe3fa
Source dataset
uspto-grants-1987_09
Patent number
US04690946

Reaction notes

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