Phenyl Isothiocyanate → HCID 15049044, compound

HRID 484554Notes

Reaction equation

HRID 484554 reaction equation
[Na].[Cl-].[C:3]([CH2:6][O:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[NH3+:14])([OH:5])=[O:4].[C:15]1([N:21]=[C:22]=[S:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[C:15]1([NH:21][C:22](=[S:23])[NH:14][C@@H:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C@H:8]2[O:7][CH2:6][C:3]([OH:5])=[O:4])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7673Phenyl IsothiocyanateHCID 5360545SodiumHCID 67747384HCID 67747384, compound

Product 1

HCID 15049044HCID 15049044, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of sodium ethoxyde prepared from Na (0.046 g, 2 mmoles) and ethanol (10 ml), there were added trans-2-carboxymethoxy-cyclohexyl ammonium chloride (0.419 g, 2 mmoles) and phenylisothiocyanate (0.270 g, 2 mmoles). The mixture was refluxed for 1 hour, evaporated and the residue was dissolved in 1N NaOH (25 ml). The solution was extracted with diethyl ether (2×20 ml), the aqueous phase was acidified with HCl 18% to pH 2 and reextracted with diethyl ether (3×20 ml). The organic phase was dried with MgSO4, the drying agent was filtered off and the filtrate was evaporated in vacuo. The residue was recrystallized from a mixture of ethanol/ether. Thus, there were obtained 0.185 g (30%) of the title compound in the form of white crystals, melting point 147°-149° C.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. customevaporated
  3. dissolutionthe residue was dissolved in 1N NaOH (25 ml)
  4. extractionThe solution was extracted with diethyl ether (2×20 ml)
  5. dry with materialThe organic phase was dried with MgSO4
  6. filtrationthe drying agent was filtered off
  7. customthe filtrate was evaporated in vacuo
  8. customThe residue was recrystallized from a mixture of ethanol/ether

Sources & evidence

ORD record
ord-f37dd4a6ce37439ab66b68ecf2239187
Source dataset
uspto-grants-1993_07
Patent number
US05231216

Reaction notes

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