Dichloromethane → HCID 20262909, compound

HRID 464313Notes

Reaction equation

HRID 464313 reaction equation
[CH2:1](I)[CH2:2][CH3:3].Cl.[CH2:6]1[C:11]2[C:12](=[O:20])[C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[S:15][C:10]=2[CH2:9][CH2:8][NH:7]1.C(N(CC)CC)C.C(Cl)[Cl:29]>C(O)C.CO>[ClH:29].[CH2:1]([N:7]1[CH2:8][CH2:9][C:10]2[S:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[C:12](=[O:20])[C:11]=2[CH2:6]1)[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 336431-IodopropaneHCID 20262908HCID 20262908, compound

Product 1

HCID 20262909HCID 20262909, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 887MethanolSolvent

Procedure

A solution of 1.44 ml of n-propyl iodide in 10 ml of ethanol was added dropwise over 20 minutes to a refluxing solution of 2.50 g of 1,2,3,4-tetrahydro-10H-(1)-benzothiopyrano[3,2-c]pyridine-10-one hydrochloride, 3.5 ml of triethylamine in 10 ml of ethanol. The mixture was refluxed for four hours after which thin layer chromatography (SiO2 :CH2Cl2 with 10% methanol) showed no starting material. The solution was evaporated to dryness and the residue was partitioned between chloroform and dilute aqueous hydrogen chloride. The aqueous layer was adjusted to a pH of 8 by addition of sodium carbonate and was extracted three times with chloroform. The organic phase was washed with water, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and eluted with methylene dichloride containing 1% of ethanol. The product was dissolved in chloroform and the solution was acidified by addition of ether saturated with hydrogen chloride. More ether was added and the mixture was filtered. The product was crystallized from ethanol and dried under reduced pressure to obtain 1.75 g (60% yield) of 1,2,3,4-tetrahydro-2-n-propyl-10H-(1)-benzothiopyrano[3,2-c]pyridin-10-one hydrochloride melting at 218° to 221° C.

Workup

  1. customThe solution was evaporated to dryness
  2. customthe residue was partitioned between chloroform and dilute aqueous hydrogen chloride
  3. additionThe aqueous layer was adjusted to a pH of 8 by addition of sodium carbonate
  4. extractionwas extracted three times with chloroform
  5. washThe organic phase was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness under reduced pressure
  8. customThe residue was chromatographed over silica gel
  9. washeluted with methylene dichloride containing 1% of ethanol
  10. dissolutionThe product was dissolved in chloroform
  11. additionthe solution was acidified by addition of ether saturated with hydrogen chloride
  12. additionMore ether was added
  13. filtrationthe mixture was filtered
  14. customThe product was crystallized from ethanol
  15. customdried under reduced pressure

Sources & evidence

ORD record
ord-a1515d13b60749218542b60221ecbce7
Source dataset
uspto-grants-1985_10
Patent number
US04547507

Reaction notes

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