Chloroform → HCID 10621159, compound

HRID 704918Notes

Reaction equation

HRID 704918 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:20])[CH2:12][S:13][CH2:14][C:15]1[O:19][CH:18]=[CH:17][CH:16]=1.C([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])C.S(Cl)(Cl)=O.[CH:35](Cl)(Cl)Cl>>[N:26]1([CH2:2][C:3]2[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=2)[O:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:20])[CH2:12][S:13][CH2:14][C:15]2[O:19][CH:18]=[CH:17][CH:16]=2)[CH2:27][CH2:28][CH2:35][CH2:30][CH2:29]1

Participants

5

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 15724712HCID 15724712, compound

Product 1

HCID 10621159HCID 10621159, compoundYield 65.3%

Procedure

N-[3-(3-hydroxymethylphenoxy)propyl]-2-(furfurylthio)acetamide (6.5 g) and triethylamine (4 g) were dissolved in 200 ml of chloroform. Under ice cooling, 2.8 g of thionyl chloride was added dropwise to the solution. The mixture was stirred for 3 hours, and then the solution was washed with a saturated aqueous solution of sodium hydrogen carbonate and water, and dried. The solvent was evaporated, and the residue was dissolved in 250 ml of ethanol and refluxed with 5 g of piperidine. Five hours later, the reaction solution was concentrated. The residue was taken into ethyl acetate and washed with 5% HCl. The washing (aqueous layer) was made alkaline with potassium carbonate (solid), and again extracted with ethyl acetate. The extract was washed with water and dried. The solvent was evaporated to give 5.09 g (yield 65.3%) of N-(3-[3-(piperidinomethyl)phenoxy]propyl)-2-(furfurylthio)acetamide.

Workup

  1. washthe solution was washed with a saturated aqueous solution of sodium hydrogen carbonate and water
  2. customdried
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in 250 ml of ethanol
  5. temperaturerefluxed with 5 g of piperidine
  6. concentrationFive hours later, the reaction solution was concentrated
  7. washwashed with 5% HCl
  8. extractionagain extracted with ethyl acetate
  9. washThe extract was washed with water
  10. customdried
  11. customThe solvent was evaporated

Sources & evidence

ORD record
ord-6f06b8ea834e42c4b28eeb9ad7daf349
Source dataset
uspto-grants-1991_01
Patent number
US04988828

Reaction notes

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