Trichloroacetonitrile → HCID 86759534, compound

HRID 1748914Notes

Reaction equation

HRID 1748914 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][C:11]([O:13][CH2:14][CH2:15][O:16][CH2:17][CH3:18])=[O:12])=[CH:5][CH:4]=1)#[N:2].[Al](Br)(Br)Br.[Cl:23][C:24]([Cl:28])([Cl:27])[C:25]#[N:26]>>[Cl:23][C:24]([Cl:28])([Cl:27])[C:25]1[N:26]=[C:25]([C:24]([Cl:28])([Cl:27])[Cl:23])[N:26]=[C:1]([C:3]2[CH:4]=[CH:5][C:6]([S:9][CH2:10][C:11]([O:13][CH2:14][CH2:15][O:16][CH2:17][CH3:18])=[O:12])=[CH:7][CH:8]=2)[N:2]=1

Participants

4

Reactant 3

HCID 11011TrichloroacetonitrileHCID 24409Aluminum bromideHCID 22666607HCID 22666607, compound

Product 1

HCID 86759534HCID 86759534, compoundYield 86%

Procedure

A mixed solution containing 10 g of 2-ethoxyethyl 2-(4-cyanophenylthio)acetate (37.7 mmol), 0.8 g of AlBr3 and 50 g of trichloroacetonitrile was bubbled with dry HCl at room temperature. The process of reaction was checked by TLC. The reaction product was formed gradually with the lapse of time while precipitation was formed. After 24 hours, the reaction mixture was quenched and extracted with 500 mL of chloroform. The resultant product was washed with deionized water and dried over anhydrous magnesium sulfate. Volatile substances were removed from the dried product under vacuum and the target product was separated by column chromatography using hexane/ethyl acetate (3/1) as eluent (yield: 86%). Then, the product was subjected to structural analysis by NMR, FT-IR and UV-Vis. spectrophotometers.

Workup

  1. customwas bubbled with dry HCl at room temperature
  2. customThe process of reaction
  3. customThe reaction product was formed gradually with the lapse of time while precipitation
  4. customwas formed
  5. customthe reaction mixture was quenched
  6. extractionextracted with 500 mL of chloroform
  7. washThe resultant product was washed with deionized water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customVolatile substances were removed from the dried product under vacuum
  10. customthe target product was separated by column chromatography

Sources & evidence

ORD record
ord-75e365dfd39c4e8c8d9d6e5ef0c234b5
Source dataset
uspto-grants-2015_10
Patent number
US09152041B2

Reaction notes

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