Propyl mercaptan → HCID 10999654, compound

HRID 1385510Notes

Reaction equation

HRID 1385510 reaction equation
[CH2:1]([SH:4])[CH2:2][CH3:3].[H-].[Na+].Cl[C:8]1[C:13]([Cl:14])=[CH:12][C:11]([C:15]([F:18])([F:17])[F:16])=[CH:10][N:9]=1>C1COCC1>[Cl:14][C:13]1[C:8]([S:4][CH2:1][CH2:2][CH3:3])=[N:9][CH:10]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:12]=1

Participants

5

Reactant 3

HCID 7848Propyl mercaptanHCID 24758Sodium hydrideHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridine

Product 1

HCID 10999654HCID 10999654, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
27.5 °C

Procedure

23.8 g (0.313 mol) of 1-propanethiol were added in the course of 30 minutes to a mixture of 7.9 g (0.313 mol) of 95% pure sodium hydride in 200 ml of THF while flushing with nitrogen and stirring, a temperature of 25-30° C. being maintained by means of cooling. After the mixture had been stirred for 1 hour, 54 g (0.25 mol) of 2,3-dichloro-5-trifluoromethylpyridine in 50 ml THF were added at 25-30° C. in the course of 20 minutes with stirring, and stirring was continued for 10 hours at 23° C. The reaction mixture was concentrated in vacuo, taken up in methylene chloride, extracted with 0.5 N sodium hydroxide solution, dried over magnesium sulfate and concentrated, yielding 63.5 g (99.4%) of the title compound of nD23=1.5120.

Workup

  1. customwhile flushing with nitrogen
  2. temperatureof cooling
  3. stirringAfter the mixture had been stirred for 1 hour
  4. stirringwith stirring
  5. stirringstirring
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. extractionextracted with 0.5 N sodium hydroxide solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d6c3a044829f433bbec9951756089fa2
Source dataset
uspto-grants-2001_07
Patent number
US06262273B1

Reaction notes

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