Ethanethiol → HCID 13882884, compound

HRID 542120Notes

Reaction equation

HRID 542120 reaction equation
[CH2:1]([SH:3])[CH3:2].[F:4][C:5]([F:23])([F:22])[C:6]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10](Cl)[CH:9]=[C:8]([C:18]([F:21])([F:20])[F:19])[N:7]=1.[O-:24]CC.[Na+].[Na].C1C=C(Cl)C=C(C(OO)=O)C=1>C(O)C>[F:4][C:5]([F:23])([F:22])[C:6]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]([S:3]([CH2:1][CH3:2])=[O:24])[CH:9]=[C:8]([C:18]([F:21])([F:20])[F:19])[N:7]=1

Participants

7

Reactant 5

HCID 6343EthanethiolHCID 70297m-Chloroperbenzoic acidHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 138828774-Chloro-2,6-bis-trifluoromethyl-nicotinic acid ethyl ester

Product 1

HCID 13882884HCID 13882884, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

Ethanethiol (5.33 ml, 0.072 mol) followed by 14.72 g (0.046 mol) of product of Example 19 was added to a solution of sodium ethoxide prepared from 1.66 g (0.072 mol) of sodium in 100 ml of ethanol and stirred at reflux overnight. The reaction mixture was filtered, poured into 200 ml of water, extracted with ether, washed with 10% NaOH, dried (MgSO4) and concentrated in vacuo to 9.45 g of yellow oil. This oil in 150 ml of CH2Cl2 was cooled to 5° C. and 3.73 g (0.022 mol) of MCPBA was added. Reaction was monitored by TLC. The reaction mixture was filtered, washed with NaHCO3, dried (MgSO4) and concentrated in vacuo to give 5.06 g of yellow oil. This was purified by HPLC using 10% ethyl acetate/cyclohexane as eluting solvent to give 3.81 g (65.6%) of an oil. A portion (1.71 g) of this oil was kugelhohr distilled at 22 Pa, pot temperature 95° C., affording 1.45 g of product as a clear oil, nD25 1.4575.

Workup

  1. temperatureat reflux overnight
  2. filtrationThe reaction mixture was filtered
  3. additionpoured into 200 ml of water
  4. extractionextracted with ether
  5. washwashed with 10% NaOH
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo to 9.45 g of yellow oil
  8. customReaction
  9. filtrationThe reaction mixture was filtered
  10. washwashed with NaHCO3
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2123c353fe994b17b7cf1c94f41ea3c5
Source dataset
uspto-grants-1987_04
Patent number
US04655816

Reaction notes

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