Benzoyl chloride → HCID 13728894, compound

HRID 2231829Notes

Reaction equation

HRID 2231829 reaction equation
C(Cl)(=O)C1C=CC=CC=1.[S-:10][C:11]#[N:12].[NH4+].[NH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH3:22])=[CH:19][C:20]=1[OH:21].[OH-].[Na+]>CC(C)=O>[OH:21][C:20]1[CH:19]=[C:18]([CH3:22])[CH:17]=[CH:16][C:15]=1[NH:14][C:11]([NH2:12])=[S:10]

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 15666Ammonium thiocyanateHCID 760822-Amino-5-methylphenol

Product 1

HCID 13728894HCID 13728894, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

0.2 mole of benzoyl chloride is added dropwise to a solution of 0.22 mole of ammonium thiocyanate in 100 ml of anhydrous acetone. The mixture is boiled to reflux for 5 minutes after the addition is complete, and a solution of 0.2 mole of 6-amino-m-cresol in 50 ml of anhydrous acetone is then added dropwise so as to maintain gentle refluxing. Stirring and heating are continued for 5 minutes after the addition, the reaction mixture is poured into 1.5 l of ice-cold water, and the crystals obtained are drained and suspended in 300 ml of 10% strength sodium hydroxide solution. The mixture is is brought to boiling for 10 minutes, and the solution is filtered on glass wool and acidified strongly with concentrated hydrochloric acid. The solution is brought back to pH 8 with ammonia solution. The crystals which precipitate on cooling are drained, washed with water and recrystallized in ethanol. (M.p. 175°-7° C.) Yld: 65%.

Workup

  1. temperatureto reflux for 5 minutes
  2. additionafter the addition
  3. temperatureto maintain gentle refluxing
  4. temperatureheating
  5. additionafter the addition
  6. customthe crystals obtained
  7. waitto boiling for 10 minutes
  8. filtrationthe solution is filtered on glass wool
  9. customThe crystals which precipitate
  10. temperatureon cooling
  11. washwashed with water
  12. customrecrystallized in ethanol

Sources & evidence

ORD record
ord-71c2580e054a4023ab342005ac1884ec
Source dataset
uspto-grants-1988_11
Patent number
US04785008

Reaction notes

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