Pyridine → HCID 19801956, compound

HRID 1646271Notes

Reaction equation

HRID 1646271 reaction equation
[Cl:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][C:5](Cl)=[O:6].[CH:10]1([SH:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.N1C=CC=CC=1>C1(C)C=CC=CC=1.C(OCC)C>[Cl:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][C:5]([S:16][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:6]

Participants

6

Reactant 3

HCID 1049PyridineHCID 15290CyclohexanethiolHCID 19801962HCID 19801962, compound

Product 1

HCID 19801956HCID 19801956, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

4.0 g of 4-chloro-4,4-difluorobutyryl chloride are added dropwise over the course of 30 minutes to a solution of 2.6 g of cyclohexyl mercaptan and 4.5 g of pyridine in 50 ml of toluene at 0° C. The reaction mixture is stirred at RT for 16 hours and then diluted with 150 ml of diethyl ether and subsequently washed with 50 ml each of 1N HCl, saturated NaHCO3 and saturated NaCl solution. The organic phase is then dried over MgSO4, filtered and evaporated. The resulting crude product is distilled at +90° C./5 mbar. 3.8 g of S-cyclohexyl 4-chloro-4,4-difluorothiobutyrate are obtained as an oil, nD23 : 1.4748.

Workup

  1. washsubsequently washed with 50 ml each of 1N HCl, saturated NaHCO3 and saturated NaCl solution
  2. dry with materialThe organic phase is then dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. distillationThe resulting crude product is distilled at +90° C./5 mbar

Sources & evidence

ORD record
ord-32b64a4a66184f2286896be9ecab2987
Source dataset
uspto-grants-1993_01
Patent number
US05179121

Reaction notes

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