1-Propanol → HCID 13101160, compound

HRID 543284Notes

Reaction equation

HRID 543284 reaction equation
Cl[C:2]1[S:3][C:4](Cl)=[C:5]2[C:11]=1[C:10](=[O:12])[C:9]1=[CH:13][S:14][CH:15]=[C:8]1[C:7](=[O:16])[NH:6]2.C([O-])=O.[NH4+].C(O)CC>[Pd].O>[CH:2]1[S:3][CH:4]=[C:5]2[C:11]=1[C:10](=[O:12])[C:9]1=[CH:13][S:14][CH:15]=[C:8]1[C:7](=[O:16])[NH:6]2

Participants

6

Reactant 3

HCID 10311-PropanolHCID 2723923Ammonium formateHCID 13766010HCID 13766010, compound

Product 1

HCID 13101160HCID 13101160, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 125 g (0.411 mole) of 1,3-dichloro-4,5-dihydrodithieno[3,4-b:3',4'-e]azepine-5,9-dione, 125 g (1.982 moles) of ammonium formate, 50 g of 5% strength Pd/C, 50 g of active carbon, 3.125 l of propanol and 165 ml of water was refluxed for 3 hours, while stirring, after which 2.5 l of solvent were distilled off under about 100 mbar, while stirring. The residue was poured onto 3 l of ice water, and the resulting suspension was acidified with concentrated hydrochloric acid, while stirring. Stirring was continued for a further hour, after which the mixture was filtered under suction and the residue was added to 1.8 l of dimethylformamide. The stirred mixture was heated at 100° C. and then filtered again under suction. The residue (Pd/C and active carbon) was washed with 5 times 100 ml of hot dimethylformamide. The original dimethylformamide mother liquor was combined with the dimethylformamide used for washing, and the still warm combined solutions were poured onto 9 l of cold water, while stirring. The precipitate formed during this procedure was filtered off under suction, washed with water and dried at 50° C., in a drying oven under reduced pressure. 80.6 g (83% OF 4,5-dihydrodithieno[3,4-b:3',4'-e]azepine-5,9-dione were obtained in the form of beige crystals of melting point 268.5°-271° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. distillationafter which 2.5 l of solvent were distilled off under about 100 mbar
  3. stirringwhile stirring
  4. additionThe residue was poured onto 3 l of ice water
  5. stirringwhile stirring
  6. stirringStirring
  7. waitwas continued for a further hour
  8. filtrationafter which the mixture was filtered under suction
  9. additionthe residue was added to 1.8 l of dimethylformamide
  10. filtrationfiltered again under suction
  11. washThe residue (Pd/C and active carbon) was washed with 5 times 100 ml of hot dimethylformamide
  12. washfor washing
  13. additionthe still warm combined solutions were poured onto 9 l of cold water
  14. stirringwhile stirring
  15. customThe precipitate formed during this procedure
  16. filtrationwas filtered off under suction
  17. washwashed with water
  18. customdried at 50° C., in a drying oven under reduced pressure

Sources & evidence

ORD record
ord-a3048d198d424a1a947b6506d7c43378
Source dataset
uspto-grants-1987_04
Patent number
US04661591

Reaction notes

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