Hydrochloric Acid → HCID 18822972, compound

HRID 1859376Notes

Reaction equation

HRID 1859376 reaction equation
[S-:1][C:2]#[N:3].[K+].[C:5](Cl)(=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1.[CH2:16]([NH:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19].Cl>CC(C)=O>[CH2:16]([N:20]([CH2:21][CH2:22][CH2:23][CH3:24])[C:2]([NH:3][C:5](=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1)=[S:1])[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8148DibutylamineHCID 74374m-Anisoyl chlorideHCID 516872Potassium thiocyanate

Product 1

HCID 18822972HCID 18822972, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 38.87 g (0.40 mol) of potassium thiocyanate in 630 ml of acetone was added dropwise over 15 min, 68.24 g (0.40 mol) m-anisoyl chloride. The mixture was heated to reflux and maintained at reflux for 20 mins. To this mixture was added 51.7 g (0.40 mol) of dibutylamine over 10 min. The mixture was stirred overnight. The mixture was added to a mixture of 103 ml of conc. HCl in 840 ml of ice water. The oily residue was extracted with methylene chloride, dried over magnesium sulfate and concentrated. The yield of product was 94.62% and was used without further purification. Anal. Calcd. for C17H26N2O2S: C, 63.3; H, 8.1, N, 8.7; S, 9.9. Found: C, 62.54; H, 8.38; N, 8.66: S, 9.19.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturemaintained
  4. temperatureat reflux for 20 mins
  5. extractionThe oily residue was extracted with methylene chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customwas used without further purification

Sources & evidence

ORD record
ord-63e8217cd0c24252a9404d9a004eccb9
Source dataset
uspto-grants-2003_03
Patent number
US06528223B1

Reaction notes

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