HCID 21279521, compound → HCID 21279508, compound

HRID 2291216Notes

Reaction equation

HRID 2291216 reaction equation
[CH2:1]([S:8][C:9]1[N:13]=[C:12]([S:14][CH:15]([CH3:19])[C:16](O)=[O:17])[NH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C>[CH2:1]([S:8][C:9]1[N:13]=[C:12]2[S:14][CH:15]([CH3:19])[C:16](=[O:17])[N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 21279521HCID 21279521, compound

Product 1

HCID 21279508HCID 21279508, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of stage (a) (57.9 g) was added portionwise to polyphosphoric acid (250 ml) at about 100° C. with stirring. Heating was continued for 30 minutes and the solution was then added to ice-water (1 l) and ethyl acetate (300 ml). The ethyl acetate solution was separated, and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with aqueous bicarbonate and water, dried and run down to give 49.3 g of crude product. Recrystallisation from ethanol gave 45.1 g of desired product, mp 85°-87° C.

Workup

  1. temperatureHeating
  2. customThe ethyl acetate solution was separated
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. washwashed with aqueous bicarbonate and water
  5. customdried
  6. customto give 49.3 g of crude product
  7. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-50ee2d48c8e34b528b6de0e485df1e1b
Source dataset
uspto-grants-1989_01
Patent number
US04795483

Reaction notes

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