Phosphorus oxychloride → HCID 15885623, compound

HRID 1108342Notes

Reaction equation

HRID 1108342 reaction equation
[C:1]([NH:4][CH:5]1[CH2:22][CH2:21][C:8]2=[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[S:10][C:11]([S:12][CH:13]([CH3:15])[CH3:14])=[C:7]2[C:6]1=[O:23])(=O)[CH3:2].P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH:13]([S:12][C:11]1[S:10][C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:8]2[CH2:21][CH2:22][C:5]3[N:4]=[C:1]([CH3:2])[O:23][C:6]=3[C:7]=12)([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12043500HCID 12043500, compound

Product 1

HCID 15885623HCID 15885623, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 5-acetylamino-4,5,6,7-tetrahydro-3-isopropylthio-4-oxobenzo[c]thiophene-1-carboxylate (1.00 g), phosphorus oxychloride (1.29 g) and toluene (30 ml) was refluxed under heating for 1.5 hours; the solution obtained was concentrated under reduced pressure, diluted with a saturated aqueous solution of sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with water and dried (MgSO4), after which the solvent was distilled off to yield ethyl 4,5-dihydro-8-isopropylthio-2-methylthieno[3,4-g]benzoxazole-6-carboxylate (0.95 g, 100%), which was then recrystallized from ethyl acetate-hexane. Yellow prisms. Melting point 62-63° C.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 1.5 hours
  3. customthe solution obtained
  4. concentrationwas concentrated under reduced pressure
  5. additiondiluted with a saturated aqueous solution of sodium hydrogen carbonate
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materialdried (MgSO4)
  9. distillationafter which the solvent was distilled off

Sources & evidence

ORD record
ord-0f7b6488e257471a8315938676d3dab7
Source dataset
uspto-grants-2000_05
Patent number
US06066658

Reaction notes

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