Triethylamine → HCID 178503917, compound

HRID 2290374Notes

Reaction equation

HRID 2290374 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][CH:10]([CH3:19])[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12].[C:20]([N:22]=[C:23](SC)[S:24][CH3:25])#[N:21]>CO>[C:20]([N:22]=[C:23]([S:24][CH3:25])[NH:9][CH:10]([CH3:19])[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12])#[N:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 2046302-Amino-1-phenylpropan-1-one;hydrochloride

Product 1

HCID 178503917HCID 178503917, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethylamine (1 ml) was added to a solution of 2-aminopropiophenone hydrochloride (0.93 g) and dimethyl cyanodithioimidocarbonate (0.73 g) in methanol (3 ml), and the mixture was refluxed for 15 minutes and evaporated under reduced pressure. The residue was dissolved in chloroform and the solution was washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue was dissolved in a small amount of ethyl acetate and diluted with diisopropyl ether. The resultant precipitates were collected by filtration, washed with diisopropyl ether and dried to give 2-(3-cyano-2-methyl-1-isothioureido)propiophenone (0.99 g).

Workup

  1. temperaturethe mixture was refluxed for 15 minutes
  2. customevaporated under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform
  4. washthe solution was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in a small amount of ethyl acetate
  8. additiondiluted with diisopropyl ether
  9. customThe resultant precipitates
  10. filtrationwere collected by filtration
  11. washwashed with diisopropyl ether
  12. customdried

Sources & evidence

ORD record
ord-cca13f9a87e649cfb24b78ae9992c867
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

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