Ammonium formate → HCID 18947051, compound

HRID 1769079Notes

Reaction equation

HRID 1769079 reaction equation
C([O-])=O.[NH4+].Cl[C:6]1[S:7][C:8](Cl)=[C:9]2[CH2:13][N:12]([S:14]([C:17]3[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH2:11][C:10]=12>CO.[Pd]>[S:14]([N:12]1[CH2:13][C:9]2=[CH:8][S:7][CH:6]=[C:10]2[CH2:11]1)([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:15])=[O:16]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 18947062HCID 18947062, compound

Product 1

HCID 18947051HCID 18947051, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

28 g of 10% palladium-on-charcoal containing 50% water and then 96 g (1.52 mol) of ammonium formate are added, under a nitrogen atmosphere, to a solution of 28.34 g (0.81 mol) of 1,3-dichloro-5-tosyl-5,6-dihydro-4H-thieno[3,4-c]pyrrole in 800 ml of methanol. The mixture is heated at reflux for 3 hours, 28 g of wet palladium-on-charcoal are then added and reflux is maintained for 24 hours. After filtration through diatomaceous earth, the filtrate is evaporated to dryness and the residue is recrystallized from methanol. 16.64 g of a white solid are obtained. Yield 73%. Melting point: 125°-127° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 3 hours
  3. temperaturereflux
  4. temperatureis maintained for 24 hours
  5. filtrationAfter filtration through diatomaceous earth
  6. customthe filtrate is evaporated to dryness
  7. customthe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-15262facf260490f92f777d682358cb6
Source dataset
uspto-grants-1995_01
Patent number
US05380742

Reaction notes

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