Phosgene → HCID 20215183, compound

HRID 1905763Notes

Reaction equation

HRID 1905763 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH2:15][O:16][CH3:17])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][C:13]#[N:14])[NH2:5].[C:18](Cl)(Cl)=[O:19]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([N:5]=[C:18]=[O:19])[CH:6]=[C:7]([CH2:15][O:16][CH3:17])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][C:13]#[N:14]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 20215188HCID 20215188, compound

Product 1

HCID 20215183HCID 20215183, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

3-Chloro-4-(3-cyanopropyloxy)-5-methoxymethylaniline (2.55 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-chloro-4-(3-cyanopropyloxy)-5-methoxymethylphenyl isocyanate (2.80 g). The thus obtained crude substance was added to a toluene solution (50 ml) containing triethylamine (1.0 g) and isopropanol (1.0 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 isopropyl N-[3-chloro-4-(3-cyanopropyloxy)-5-methoxymethylphenyl]carbamate (Compound No. 6) (2.70 g) in a yield of 79.2%. nD20.0 1.5196.

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-6d54d9a2c18941d3b93fb13cad753344
Source dataset
uspto-grants-1987_03
Patent number
US04647584

Reaction notes

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