Propyl mercaptan → HCID 68497666, compound

HRID 658360Notes

Reaction equation

HRID 658360 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:20])[N:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]([CH2:12]O)=[CH:10][CH:11]=1)=[O:5])[CH3:2].P(Br)(Br)Br.C(=O)([O-])[O-].[K+].[K+].[CH2:31]([SH:34])[CH2:32][CH3:33]>ClCCl.CN(C=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:20])[N:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]([CH2:12][S:34][CH2:31][CH2:32][CH3:33])=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 7848Propyl mercaptanHCID 11430Potassium CarbonateHCID 24614Phosphorus tribromideHCID 68497201HCID 68497201, compound

Product 1

HCID 68497666HCID 68497666, compoundYield 25.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

1,2-dihydro-6-hydroxymethyl-2-oxo-1-phenylpyridine-3-carboxylic acid ethyl ester (5.0 g, 18 mmol) was dissolved in dichloromethane (100 mL), and phosphorus tribromide (1.95 g, 7.2 mol) was added to this solution at −20° C. under a nitrogen atmosphere. The mixture was allowed to react for 4 hours. The reaction mixture was poured into water and a liquid separation was subjected. The organic layer was washed with an aqueous sodium bicarbonate solution and water, dried, and concentrated to obtain 3.30 g of a crude desired product. This crude product was dissolved in N,N′-dimethylformamide (30 mL), and potassium carbonate (2.0 g, 14 mmol) and propyl mercaptan (1.1 g, 14 mmol) were added thereto. The mixture was allowed to react for 2 hours at room temperature. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with an aqueous solution of citric acid and water, dried, and concentrated. Thus obtained oily product was purified by column chromatography (elution solvent: hexane/ethyl acetate=3/2) to obtain 1.17 g of a desired product (yield: 20%, two stages).

Workup

  1. customto react for 4 hours
  2. customa liquid separation
  3. washThe organic layer was washed with an aqueous sodium bicarbonate solution and water
  4. customdried
  5. concentrationconcentrated
  6. customto obtain 3.30 g of a crude desired product
  7. customto react for 2 hours at room temperature
  8. extractionextracted with ethyl acetate
  9. washThe organic layer was washed with an aqueous solution of citric acid and water
  10. customdried
  11. concentrationconcentrated
  12. customThus obtained oily product was purified by column chromatography (elution solvent: hexane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-f7651cf3a49a432ba2ffc0562782a7cd
Source dataset
uspto-grants-2011_12
Patent number
US08076487B2

Reaction notes

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