Acetone → HCID 178458061, compound

HRID 859723Notes

Reaction equation

HRID 859723 reaction equation
[Na].[C:2]([NH:5][NH2:6])([NH2:4])=[NH:3].Cl.[C:8]1([N:14]=[C:15]=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:17][C:18]([CH3:20])=O>>[NH:14]([C:15]([NH:3][C:2]([NH:5][N:6]=[C:18]([CH3:20])[CH3:17])=[NH:4])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 7672Phenyl isocyanateHCID 5360545SodiumHCID 178418668HCID 178418668, compound

Product 1

HCID 178458061HCID 178458061, compound

Procedure

To a suspension of sodium (19 g, 0.82 mol) in acetone (1000 mL) and was added aminoguanidine hydrochloride (100 g, 0.91 mol) in portions. The mixture was refluxed for 60 minutes. The heating bath was removed, and phenyl isocyanate (78.4 g, 0.65 mol) was added dropwise during 30 minutes. The mixture was refluxed for another 30 minutes. The mixture was poured into ice water (2.5 L). The oil solidified at room temperature during an overnight stirring. The solid was filtered and washed with petroleum ether to afford the product as a yellow solid (150 g, 70%.

Workup

  1. temperatureThe mixture was refluxed for 60 minutes
  2. customThe heating bath was removed
  3. temperatureThe mixture was refluxed for another 30 minutes
  4. filtrationThe solid was filtered
  5. washwashed with petroleum ether

Sources & evidence

ORD record
ord-e2f00a18565c4c90872a974ac963d2aa
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

Loading…