Acetone → HCID 22908118, compound

HRID 1379804Notes

Reaction equation

HRID 1379804 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].[S-:12][C:13]#[N:14].[NH4+:15].[CH3:16][C:17]([CH3:19])=O>>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:14][C:13]([NH:15][CH:17]2[CH2:19][CH2:16]2)=[S:12])=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 3

HCID 180AcetoneHCID 15666Ammonium thiocyanateHCID 801724-Cyanobenzoyl chloride

Product 1

HCID 22908118HCID 22908118, compound

Procedure

4-Cyanobenzoyl chloride (20 g) was added in portions to a solution of ammonium thiocyanate (9.2 g) in acetone (200 ml) at room temperature, followed by heating under reflux for 20 minutes. The reaction mixture was ice-cooled, and after removal of the insoluble substance by filtration, the filtrate was evaporated under reduced pressure. To the resulting residue were added toluene (100 ml) and cyclopropylamine (7.6 g) successively, followed by stirred for 30 minutes. The precipitated crystals were collected by filtration and recrystallized from ethyl acetate to give 1-(4-cyanobenzoyl)-3-cyclopropylthiourea (20 g) as a colorless powder.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 20 minutes
  3. temperaturecooled
  4. customafter removal of the insoluble substance
  5. filtrationby filtration
  6. customthe filtrate was evaporated under reduced pressure
  7. additionTo the resulting residue were added toluene (100 ml) and cyclopropylamine (7.6 g) successively
  8. filtrationThe precipitated crystals were collected by filtration
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-cbc5a240507546dfaf537a7feebef837
Source dataset
uspto-grants-1997_09
Patent number
US05672712

Reaction notes

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