Hydrochloric Acid → HCID 19897013, compound

HRID 1196980Notes

Reaction equation

HRID 1196980 reaction equation
Cl.[CH2:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12](=O)[CH:13]([NH:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH3:14])=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5].[O-:23][C:24]#[N:25].[K+].Cl>O>[CH2:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:25][C:24](=[O:23])[N:15]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[C:13]=2[CH3:14])=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11378442Potassium cyanateHCID 19897008HCID 19897008, compound

Product 1

HCID 19897013HCID 19897013, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

4'-n-Butyl-2-cyclohexylaminopropiophenone hydrochloride (1768 mg, 5.5 mmol) was suspended in water (30 ml), and potassium cyanate (914 mg, 11.3 mmol) in water (10 ml) was added thereto. The aqueous mixture was heated under reflux for one hour under nitrogen atomosphere, added with conc. hydrochloride (2 ml), and heated under reflux an additional one hour. The reaction mixture was extracted with dichloromethane, and the extract was washed with 10% hydrochloride, and dried over anhydrous magnesium sulfate. Evaporation of the solvent under vacuum and recrystalization from ethyl acetate gave the title compound. Yield: 155 mg (9%), m.p. 236° C.

Workup

  1. temperatureThe aqueous mixture was heated
  2. temperatureunder reflux for one hour under nitrogen atomosphere
  3. temperatureheated
  4. temperatureunder reflux an additional one hour
  5. extractionThe reaction mixture was extracted with dichloromethane
  6. washthe extract was washed with 10% hydrochloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customEvaporation of the solvent
  9. customunder vacuum and recrystalization from ethyl acetate

Sources & evidence

ORD record
ord-967e57d5d9b14edf9d80caddeb19b762
Source dataset
uspto-grants-1992_05
Patent number
US05116858

Reaction notes

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