Triethylamine → Carbamothioic chloride, (2-chlorophenyl)propyl-

HRID 1730028Notes

Reaction equation

HRID 1730028 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[NH:4][CH2:5][CH2:6][CH3:7].C(N(CC)CC)C.[C:19](Cl)([Cl:21])=[S:20]>CCOCC>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[N:4]([CH2:5][CH2:6][CH3:7])[C:19]([Cl:21])=[S:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 151785102-Chloro-N-propylaniline

Product 1

HCID 21319512Carbamothioic chloride, (2-chlorophenyl)propyl-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 25.4 g. 2-chloro-N-propylaniline and 15.15 g. dry triethylamine in 200 ml. dry ether was added to a solution of 13 ml. thiophosgene in 200 ml. of the same solvent at -20° C. The reaction mixture was allowed to warm to room temperature and then filtered, the filtered solid being washed with ether. The ethereal extract was added to the ethereal liquor and after drying over sodium sulphate, was evaporated to give a dark oil. On standing further solid precipitated, which was then separated from the oil. The oily filtrate was distilled to give the product N-2-chlorophenyl-N-propyl(thiocarbamoyl) chloride, b.p. 119°-120° C./0.4 mm. Hg.

Workup

  1. customat -20° C
  2. filtrationfiltered
  3. washthe filtered solid being washed with ether
  4. extractionThe ethereal extract
  5. additionwas added to the ethereal liquor
  6. dry with materialafter drying over sodium sulphate
  7. customwas evaporated
  8. customto give a dark oil
  9. customprecipitated
  10. customwhich was then separated from the oil
  11. distillationThe oily filtrate was distilled

Sources & evidence

ORD record
ord-514a6e9ad4c54c45bf3b4095f717febf
Source dataset
uspto-grants-1976_11
Patent number
US03991071

Reaction notes

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