Water → HCID 13935723, compound

HRID 255485Notes

Reaction equation

HRID 255485 reaction equation
[CH2:1]([SH:3])[CH3:2].C(N(CC)CC)C.[Cl:11][C:12]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:13]=1[O:14][C:15]1[CH:16]=[C:17]([CH2:21][C:22](Cl)=[O:23])[CH:18]=[CH:19][CH:20]=1.O>CN(C)C(=O)C>[Cl:11][C:12]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:13]=1[O:14][C:15]1[CH:16]=[C:17]([CH2:21][C:22]([S:3][CH2:1][CH3:2])=[O:23])[CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 8471TriethylamineHCID 13630154{3-[2-Chloro-4-(trifluoromethyl)phenoxy]phenyl}acetyl chloride

Product 1

HCID 13935723HCID 13935723, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

0.7 g of ethyl mercaptan and 1.2 g of triethylamine were dissolved in 20 ml of N,N-dimethylacetamide. To the resulting solution, 3.5 g of 3-(2'-chloro 4'-trifluoromethylphenoxy)phenylacetyl chloride was dropwise added at 10° C. After completion of the dropwise addition, the reaction was allowed to proceed at room temperature for 3 hours. After completion of the reaction, 50 ml of water was added to the liquid reaction mixture, followed by extraction twice with 30 ml portions of ether. The ether layer was washed with water and dried over anhydrous sodium sulfate, followed by evaporation-removal of the ether under reduced pressure, thereby to obtain a crude product. The so-obtained crude product was subjected to purification by the silica gel column chromatography (elution was performed by using a mixed solvent of toluene and n-hexane). As a result, there was obtained 1.9 g of S-ethyl 3-(2'-chloro-4'-trifluoromethylphenoxy)phenylthioacetate.

Workup

  1. additionAfter completion of the dropwise addition
  2. additionwas added to the liquid reaction mixture
  3. extractionfollowed by extraction twice with 30 ml portions of ether
  4. washThe ether layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customfollowed by evaporation-removal of the ether under reduced pressure
  7. customto obtain a crude product
  8. customThe so-obtained crude product
  9. customwas subjected to purification by the silica gel column chromatography (
  10. washelution

Sources & evidence

ORD record
ord-456dfd1900274e738816f25c47726d8b
Source dataset
uspto-grants-1987_10
Patent number
US04698094

Reaction notes

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