Water → HCID 18947049, compound

HRID 1769087Notes

Reaction equation

HRID 1769087 reaction equation
O.[CH:2]([O-:4])=[O:3].[NH4+].Cl[C:7]1[S:8][C:9](Cl)=[C:10]2[C:14](=C=O)[N:13](OC(C)(C)C)[CH2:12][C:11]=12>CO.[Pd]>[CH3:9][C:10]([CH3:14])([O:3][C:2]([N:13]1[CH2:12][C:11]2=[CH:7][S:8][CH:9]=[C:10]2[CH2:14]1)=[O:4])[CH3:11]

Participants

6

Reactant 3

HCID 962WaterHCID 2723923Ammonium formateHCID 86748382HCID 86748382, compound

Product 1

HCID 18947049HCID 18947049, compoundYield 134.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

17.6 g of 10% palladium-on-charcoal containing 50% of water and then 41.6 g (600 mmol) of ammonium formate are added to a solution of 8.82 g (30 mmol) of 1,3-dichloro-5(1,1-dimethylethoxy)-carbonyl-5,6-dihydro-4H -thieno[3,4-c]pyrrole in 75 ml of methanol. The mixture is heated at reflux for 24 hours and it is then cooled, filtered through a Celite column, rinsed with twice 50 ml of dichloromethane and evaporated to dryness. The residue is taken up in 100 ml of dichloromethane, filtered and evaporated to dryness. There are obtained 4.54 g of an oily product which crystallizes slowly. Yield 68%. Melting point: 36°-38° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 24 hours
  3. temperatureit is then cooled
  4. filtrationfiltered through a Celite column
  5. washrinsed with twice 50 ml of dichloromethane
  6. customevaporated to dryness
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-510fe539fc74480fa50aff71d0029a35
Source dataset
uspto-grants-1995_01
Patent number
US05380742

Reaction notes

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