Phosphorus sulfide (P2S5) → HCID 86595218, compound

HRID 1726921Notes

Reaction equation

HRID 1726921 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([N:8]([CH3:13])[CH2:9][C:10]([OH:12])=[O:11])=O)=[CH:4][CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:17]>C1(C)C=CC=CC=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([N:8]([CH3:13])[CH2:9][C:10]([OH:12])=[O:11])=[S:17])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 16773647HCID 16773647, compound

Product 1

HCID 86595218HCID 86595218, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 14817Phosphorus sulfide (P2S5)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a slurry of 4.54 g of 4-chlorobenzoyl methyl glycine (20 mmol) in 60 ml of toluene under an atmosphere of nitrogen was added 0.89 g (20 mmol) of phosphorus pentasulfide. The reaction was heated to 90° C. for 3 hours. An additional 0.18 g of phosphorus pentasulfide was added, and the reaction was heated for an additional 1 hour, then cooled to room temperature. The product was filtered, the slurry was washed with ethyl acetate, and the combined filtrates were run through silica gel on Gelite, then stripped. The product was chromatographed on a silica gel column to give 3.3 g (68% yield) of 4-chlorothiobenzoyl methylglycine, melting point 72-73° C.

Workup

  1. temperaturethe reaction was heated for an additional 1 hour
  2. temperaturecooled to room temperature
  3. filtrationThe product was filtered
  4. washthe slurry was washed with ethyl acetate
  5. customThe product was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-f62a593744834e3a90f6c49f0a87677a
Source dataset
uspto-grants-2009_02
Patent number
US07494996B2

Reaction notes

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