Tributylamine → HCID 13101160, compound

HRID 543285Notes

Reaction equation

HRID 543285 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(N(CCCC)CCCC)CCC.[H][H]>[Pd].C(O)CC>[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 7622TributylamineHCID 13766010HCID 13766010, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13101160HCID 13101160, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10311-PropanolSolvent2×

Procedure

A mixture of 5.0 g (0.0164 mole) of 1,3-dichloro-4,5-dihydrodithieno[3,4-b:3',4'-e]azepine-5,9-dione, 4 g of 5% strength Pd/C, 6.3 g (0.034 mole) of tributylamine and 300 ml of propanol was stirred in a hydrogen atmosphere at 80° C. When absorption of hydrogen was complete (after 5 hours), the hot mixture was filtered and the filtrate was poured onto ice water. The resulting suspension was acidified with concentrated hydrochloric acid, and the mixture was then stirred for a short time and filtered under suction. The residue from filtration of the crude reaction mixture was washed several times with hot dimethylformamide. The dimethylformamide used for washing was poured onto ice water, and the precipitate formed was filtered off under suction. The solid thus obtained was combined with the solid product obtained from the propanol filtrate. The total solid product was washed with water and then dried at 50° C. in a drying oven under reduced pressure. 2.9 g (75%) 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°-271° C.

Workup

  1. customWhen absorption of hydrogen
  2. custom(after 5 hours)
  3. filtrationthe hot mixture was filtered
  4. additionthe filtrate was poured onto ice water
  5. filtrationfiltered under suction
  6. filtrationThe residue from filtration of the crude
  7. customreaction mixture
  8. washwas washed several times with hot dimethylformamide
  9. washfor washing
  10. additionwas poured onto ice water
  11. customthe precipitate formed
  12. filtrationwas filtered off under suction
  13. customThe solid thus obtained
  14. washThe total solid product was washed with water
  15. customdried at 50° C. in a drying oven under reduced pressure

Sources & evidence

ORD record
ord-68ff66f7d98d41ec99d29bceba027f52
Source dataset
uspto-grants-1987_04
Patent number
US04661591

Reaction notes

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