Benzenepropanal → Carbamic acid, [3-phenyl-1-(phenylsulfonyl)propyl]-, phenylmethyl ester

HRID 1955684Notes

Reaction equation

HRID 1955684 reaction equation
[C:1]1([S:7]([O-:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].[C:11](=[O:21])([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH2:12].[CH:22](=O)[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(OCC)(=O)C.CCCCCC>O.C(O)=O>[CH2:14]([O:13][C:11]([NH:12][CH:22]([S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 7707BenzenepropanalHCID 12136Benzyl carbamateHCID 2723840Benzenesulfinic acid, sodium saltHCID 21226206Ethyl acetate hexane

Product 1

HCID 10597651Carbamic acid, [3-phenyl-1-(phenylsulfonyl)propyl]-, phenylmethyl ester

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of sodium benzenesulfinate (10 g, 60.9 mmol) and benzyl carbamate (9.21 g, 60.9 mmol) in water (40 mL) was added hydrocinnamaldehyde (8.8 mL, 67 mmol) in formic acid (10 mL). The mixture was heated at 70° C. for 1 hour, then permitted to cool to room temperature overnight. The product crystallized out; it was filtered and recrystallized from hot isopropanol, giving 23 g (100%) yield. TLC: (30% ethyl acetate/hexane) Rf =0.37.

Workup

  1. temperatureto cool to room temperature overnight
  2. customThe product crystallized out
  3. filtrationit was filtered
  4. customrecrystallized from hot isopropanol
  5. customgiving 23 g (100%)
  6. customyield

Sources & evidence

ORD record
ord-7d803cb20dd94c36b1f8946691067151
Source dataset
uspto-grants-1998_07
Patent number
US05776718

Reaction notes

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