Acetone → HCID 86734724, compound

HRID 2397920Notes

Reaction equation

HRID 2397920 reaction equation
[Na].S(O)(O)(=O)=[O:3].[NH:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([NH2:20])=[NH:19])[C:8]([NH2:10])=[NH:9].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[S:30])=[CH:24][CH:23]=1.C[OH:32].[CH3:33][C:34]([CH3:36])=[O:35]>C(O)(=O)C>[C:34]([OH:32])(=[O:35])[CH3:36].[C:34]([OH:3])(=[O:35])[CH3:36].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([N:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]([C:29](=[S:30])[NH:28][C:34]2[CH:36]=[CH:27][C:22]([Cl:21])=[CH:23][CH:33]=2)[C:18]([NH2:20])=[NH:19])[C:8]([NH2:10])=[NH:9])=[S:30])=[CH:24][CH:23]=1

Participants

7

Reactant 5

HCID 180AcetoneHCID 887MethanolHCID 164804-Chlorophenyl isothiocyanateHCID 5360545Sodium2×HCID 176528103HCID 176528103, compound

Product 1

HCID 86734724HCID 86734724, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium (0.05 g, 0.02 m) is dissolved in dry acetone and 3.0 grams (0.01m) of 1,6-bis(guanidino)hexane sulfate is added. The resulting suspension is stirred for two hours at room temperature and thereafter 3.4 grams (0.02 m) of 4-chlorophenyl isothiocyanate is added. The mixture is heated at 60° for three hours, then stirred overnight at room temperature. Ten milliliters of methanol are added to decompose residual sodium. The solvent is distilled and the residue is washed by decantation with several portions of water to leave the product as the free base. The residue is dissolved in 60 ml. of warm acetic acid. The solution is cooled and the diacetate which precipitates is collected on a filter, washed with acetic acid, then recrystallized from acetic acid, M.P. 145°-148° C.

Workup

  1. temperatureThe mixture is heated at 60° for three hours
  2. stirringstirred overnight at room temperature
  3. distillationThe solvent is distilled
  4. washthe residue is washed by decantation with several portions of water
  5. customto leave the product as the free base
  6. dissolutionThe residue is dissolved in 60 ml
  7. temperatureThe solution is cooled
  8. customthe diacetate which precipitates
  9. customis collected on a filter
  10. washwashed with acetic acid
  11. customrecrystallized from acetic acid, M.P. 145°-148° C.

Sources & evidence

ORD record
ord-3629166eaae84bf681cf46106217e51b
Source dataset
uspto-grants-1977_05
Patent number
US04022962

Reaction notes

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