Phosgene → HCID 20215180, compound

HRID 1905709Notes

Reaction equation

HRID 1905709 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:9]=[C:10]([Cl:15])[C:11]=1[O:12][CH2:13][CH3:14])[NH2:8].[C:16](Cl)(Cl)=[O:17]>C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([N:8]=[C:16]=[O:17])[CH:9]=[C:10]([Cl:15])[C:11]=1[O:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 20215181HCID 20215181, compound

Product 1

HCID 20215180HCID 20215180, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

3-(2-Chloroethoxy)-4-ethoxy-5-chloroaniline (2.50 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-(2-chloroethoxy)-4-ethoxy-5-chlorophenyl isocyanate. The thus obtained crude substance was added to a toluene solution (50 ml) containing triethylamine (1.0 g) and 1-butyn-3-ol (0.75 g). The resultant mixture was allowed to stand at room temperature for 12 hours, poured into ice-water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography using a mixture of toluene and ethyl acetate as the eluent to give 1-methyl-2-propynyl N-[3-(2-chloroethoxy)-4-ethoxy-5-chlorophenyl]-carbamate (Compound No. 31) (3.27 g) in a yield of 91.6%.

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-6c44fa33634a4a078ac92e8fa6562c84
Source dataset
uspto-grants-1987_03
Patent number
US04647582

Reaction notes

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