Water → S-1-methylethyl 3-(2'-chloro-4'-trifluoromethylphenoxy)-phenylthioacetate

HRID 255486Notes

Reaction equation

HRID 255486 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=O)[CH:8]=[CH:9][CH:10]=1.O.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:39][CH:40]([SH:42])[CH3:41]>ClCCl>[Cl:1][C:2]1[CH:18]=[C:17]([C:19]([F:20])([F:22])[F:21])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([S:42][CH:40]([CH3:41])[CH3:39])=[O:14])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 63642-PropanethiolHCID 10868DicyclohexylcarbodiimideHCID 13607437{3-[2-Chloro-4-(trifluoromethyl)phenoxy]phenyl}acetic acid

Product 1

HCID 13607438S-1-methylethyl 3-(2'-chloro-4'-trifluoromethylphenoxy)-phenylthioacetateYield 41.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.3 g of 3-(2'-chloro-4'-trifluoromethylphenoxy)phenylacetic acid was dissolved in 30 ml of dichloromethane, and the resulting solution was cooled to below 10° C. on the water bath. Then, 2.1 g of N,N'-dicyclohexylcarbodiimide (DCC) was added, followed by addition of 0.8 g of 2-propanethiol. The reaction was allowed to proceed at room temperature for about 6 hours. After completion of the reaction, the formed solid substance was filtered off, and the filtrate was subjected to evaporation-removal of the solvent under reduced pressure to obtain a crude product. The thus 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 1.6 g of S-1-methylethyl 3-(2'-chloro-4'-trifluoromethylphenoxy)-phenylthioacetate.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe formed solid substance was filtered off
  3. customthe filtrate was subjected to evaporation-removal of the solvent under reduced pressure
  4. customto obtain a crude product
  5. customThe thus obtained crude product
  6. customwas subjected to purification by the silica gel column chromatography (
  7. washelution

Sources & evidence

ORD record
ord-cf0522b54c9c400cb0e96997afe2170b
Source dataset
uspto-grants-1987_10
Patent number
US04698094

Reaction notes

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