Water → HCID 13630155, compound

HRID 255490Notes

Reaction equation

HRID 255490 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH2:2][SH:3].C(N(CC)CC)C.[Cl:15][C:16]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:17]=1[O:18][C:19]1[CH:20]=[C:21]([CH2:25][C:26](Cl)=[O:27])[CH:22]=[CH:23][CH:24]=1.O>CN(C)C(=O)C>[Cl:15][C:16]1[CH:32]=[C:31]([C:33]([F:34])([F:36])[F:35])[CH:30]=[CH:29][C:17]=1[O:18][C:19]1[CH:20]=[C:21]([CH2:25][C:26]([S:3][CH2:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])=[O:27])[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12185Ethyl ThioglycolateHCID 13630154{3-[2-Chloro-4-(trifluoromethyl)phenoxy]phenyl}acetyl chloride

Product 1

HCID 13630155HCID 13630155, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1.2 g of ethyl thioglycolate and 1.2 g of triethylamine were dissolved in 20 ml of N,N-dimethylacetamide. To the thus obtained solution was dropwise added 3.5 g of 3-(2'-chloro-4'-trifluoromethylphenoxy)phenylacetyl chloride at 10° C. After completion of the dropwise addition, the reaction was allowed to proceed at room temperature for 3 hours to complete reaction. After completion of the reaction, 50 ml of water was added to the 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, and the ether was distilled off under reduced pressure to obtain a crude product. The obtained crude product was subjected to purification by the silica gel column chromatography to obtain 3.5 g of S-ethoxycarbonylmethyl 3-(2'-chloro-4'-trifluoromethylphenoxy)phenylthioacetate.

Workup

  1. customat 10° C
  2. additionAfter completion of the dropwise addition
  3. customto proceed at room temperature for 3 hours to complete reaction
  4. additionwas added to the reaction mixture
  5. extractionfollowed by extraction twice with 30 ml portions of ether
  6. washThe ether layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe ether was distilled off under reduced pressure
  9. customto obtain a crude product
  10. customThe obtained crude product
  11. customwas subjected to purification by the silica gel column chromatography

Sources & evidence

ORD record
ord-12af3d8969b440c48a699bee6f15bfa6
Source dataset
uspto-grants-1987_10
Patent number
US04698094

Reaction notes

Loading…