Acetone → HCID 178458061, compound

HRID 2387113Notes

Reaction equation

HRID 2387113 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, compoundYield 70%

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-ca48c3727751409cb9d7c256b36c5609
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

Loading…