Butanethiol → HCID 19351640, compound

HRID 1636432Notes

Reaction equation

HRID 1636432 reaction equation
[CH2:1]([SH:5])[CH2:2][CH2:3][CH3:4].[Na].[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][C:15](=[O:17])[C:14]([CH2:18][CH2:19][CH3:20])=[C:13](Cl)[C:12]=2[CH:22]=1>C(O)C>[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][C:15](=[O:17])[C:14]([CH2:18][CH2:19][CH3:20])=[C:13]([S:5][CH2:1][CH2:2][CH2:3][CH3:4])[C:12]=2[CH:22]=1

Participants

5

Reactant 3

HCID 8012ButanethiolHCID 5360545SodiumHCID 193516286-bromo-4-chloro-3-propyl-2H-1-benzopyran-2-one

Product 1

HCID 19351640HCID 19351640, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1-Butanethiol (0.39 ml) was added dropwise to a solution of sodium (0.08 g) in ethanol (3 ml). The solution was stirred for 1/2 hour and then added slowly to a refluxing solution of 6-bromo-4-chloro-3-propyl-2H-1-benzopyran-2-one (1 g) in ethanol (4 ml). The mixture was heated under reflux for 41/2 hours, filtered hot through kieselguhr and the filtrate allowed to cool. The precipitate was purified by silica gel column chromatography to give 6-bromo-4-butylthio-3-propyl-2H-1-benzopyran-2-one, m.p. 62-4° (compound 15)

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 41/2 hours
  3. filtrationfiltered hot through kieselguhr
  4. temperatureto cool
  5. customThe precipitate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5828695c03ec457d9291170c9157be78
Source dataset
uspto-grants-2000_03
Patent number
US06034121

Reaction notes

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