Phosphorus oxide (P4O10) → HCID 22118435, compound

HRID 1275449Notes

Reaction equation

HRID 1275449 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([S:13][CH2:14][CH2:15][C:16]([OH:18])=O)=[C:8]([CH3:19])[CH:7]=1)=[O:5])[CH3:2].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[CH2:1]([O:3][C:4]([C:6]1[C:11]([CH3:12])=[C:10]2[C:9](=[C:8]([CH3:19])[CH:7]=1)[S:13][CH2:14][CH2:15][C:16]2=[O:18])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 221184403-{[4-(Ethoxycarbonyl)-2,5-dimethylphenyl]sulfanyl}propanoic acid

Product 1

HCID 22118435HCID 22118435, compoundYield 86.3%

Conditions

Temperature
40 °C

Procedure

21.5 Grams (64 mmol) of 3-(4-ethoxycarbonyl-2,5-dimethylphenylthio)propionic acid was added to 100 g of a 20 wt % P2O5 -containing polyphosphoric acid at room temperature, and then the mixture was stirred under heat at 40° C. for 2 hours. After allowed to cool, the reaction mixture was gradually added to ice water and extracted with ethyl acetate, and an organic layer was washed with a 1 wt % sodium carbonate aqueous solution twice, with water twice and with a saturated sodium chloride aqueous solution once, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 14.6 g (yield 86%) of the titled compound.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. washan organic layer was washed with a 1 wt % sodium carbonate aqueous solution twice
  4. dry with materialwith water twice and with a saturated sodium chloride aqueous solution once, and dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-47e86db9fc68482a9d77113c1b8d00d6
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

Loading…