Phosgene → HCID 20187593, compound

HRID 1979687Notes

Reaction equation

HRID 1979687 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]>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:4]=[C:5]([N:6]=[C:14]=[O:15])[CH:7]=[C:8]([CH3:13])[C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 20187592HCID 20187592, compound

Product 1

HCID 20187593HCID 20187593, compoundYield 101.9%

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 give 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

Sources & evidence

ORD record
ord-94a9c1d3457748e8bc7b05849bf75a68
Source dataset
uspto-grants-1984_11
Patent number
US04482546

Reaction notes

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