Sodium Sulfide → HCID 14770036, compound

HRID 477921Notes

Reaction equation

HRID 477921 reaction equation
[N+:1]([CH:4]1[C:13]23S[C:6]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)([C:7](=[O:18])[N:8]2[CH2:9][CH2:10][C:11]2[CH:17]=[CH:16][S:15][C:12]=23)[CH2:5]1)([O-])=O.C[O-].[Na+].[S-2].[Na+].[Na+]>CO>[NH2:1][C:4]1[CH:5]=[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7](=[O:18])[N:8]2[C:13]=1[C:12]1[S:15][CH:16]=[CH:17][C:11]=1[CH2:10][CH2:9]2

Participants

5

Reactant 3

HCID 14804Sodium SulfideHCID 10942334Sodium MethoxideHCID 19020424HCID 19020424, compound

Product 1

HCID 14770036HCID 14770036, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

3.2 g of 4,5,9,10-tetrahydro-10-nitro-8-phenyl-8,10a-epithio-10aH-thieno[2,3-a]quinolizin-7(8H)-one was suspended in 300 ml of methanol. The suspension was treated while stirring with a solution of sodium methylate in methanol (prepared from 4.46 g of sodium and 5 ml of methanol) and subsequently with a solution of 14 g of sodium sulfide in 40 ml of methanol, whereby there results a dark solution which is held at 60° for 4 hours. After the methanol is removed by distillation in vacuo, the residue was taken up in water. The solution was extracted with chloroform and the organic phase was washed with saturated aqueous sodium chloride solution. The organic phase was dried over magnesium sulfate, evaporated in vacuo and the product was chromatographed on silica gel with toluene/acetone (9:1). There was obtained 10-amino-4,5-dihydro-8-phenyl-7H-thieno[2,3-a]quinolizin-7-one of m.p. 180.5°-181.5° (from toluene).

Workup

  1. additionThe suspension was treated
  2. customresults a dark solution which
  3. customAfter the methanol is removed by distillation in vacuo
  4. extractionThe solution was extracted with chloroform
  5. washthe organic phase was washed with saturated aqueous sodium chloride solution
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. customevaporated in vacuo
  8. customthe product was chromatographed on silica gel with toluene/acetone (9:1)

Sources & evidence

ORD record
ord-0106a8f422c54636add20b5d12698e73
Source dataset
uspto-grants-1989_12
Patent number
US04889848

Reaction notes

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