HCID 19813444, compound → HCID 19813430, compound

HRID 1031987Notes

Reaction equation

HRID 1031987 reaction equation
[CH3:1][N:2]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=1)[CH2:3][C:4]1[S:8][C:7]2[CH:9]=[CH:10][C:11]([N+:13]([O-])=O)=[CH:12][C:6]=2[CH:5]=1>C(O)C>[CH3:1][N:2]([CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=1)[CH2:3][C:4]1[S:8][C:7]2[CH:9]=[CH:10][C:11]([NH2:13])=[CH:12][C:6]=2[CH:5]=1

Participants

3

Reactant 1

HCID 19813444HCID 19813444, compound

Product 1

HCID 19813430HCID 19813430, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the product of (B) above (1.0 g) and stannous chloride dihydrate (6.07 g) in ethanol (100 ml) was heated under reflux for 8 hours and then evaporated. An excess of 20% aqueous sodium hydroxide solution was added and the mixture was extracted several times with dichloromethane. The combined organic extracts were washed with water, dried (Na2SO4) and evaporated to give an oil which was chromatographed on silica gel. Elution with dichloromethane/methanol (99:1) gave impurity and then further elution with dichloromethane/methanol (98:2) gave, after collection and evaporation of appropriate fractions, the product as an oil (0.30 g) which was used immediately in the procedure of Example 6.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hours
  3. customevaporated
  4. additionAn excess of 20% aqueous sodium hydroxide solution was added
  5. extractionthe mixture was extracted several times with dichloromethane
  6. washThe combined organic extracts were washed with water
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customto give an oil which
  10. customwas chromatographed on silica gel
  11. washElution with dichloromethane/methanol (99:1)
  12. customgave impurity
  13. washfurther elution with dichloromethane/methanol (98:2)
  14. customgave
  15. customafter collection and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-654ca07bc8724d0198ccc3b7ebef81f8
Source dataset
uspto-grants-1990_09
Patent number
US04956382

Reaction notes

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