Trichloroacetyl chloride → (5-Trichloroacetoxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile

HRID 1018891Notes

Reaction equation

HRID 1018891 reaction equation
[OH:1][N:2]=[C:3]1[S:7][C:6](=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:9]#[N:10])[CH:5]=[CH:4]1.[Cl:18][C:19]([Cl:24])([Cl:23])[C:20](Cl)=[O:21].C(N(CC)CC)C>C1COCC1>[Cl:18][C:19]([Cl:24])([Cl:23])[C:20]([O:1][N:2]=[C:3]1[S:7][C:6](=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:9]#[N:10])[CH:5]=[CH:4]1)=[O:21]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 86758612HCID 86758612, compound

Product 1

HCID 54426949(5-Trichloroacetoxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

1.0 g (4.1 mmol) of (5-Hydroxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile, prepared as described in example 7.1, are dissolved in 11 ml of THF and cooled in an ice bath. After adding 0.83 g (4.5 mmol) of trichloroacetyl chloride to the solution, 0.63 g (6.2 mmol) of triethylamine are added dropwise, keeping the temperature below 5° C. While the reaction mixture is stirred at 5° C. for 20 min, a precipitate is formed. The precipitate is filtered off and washed with THF. The filtrate is concentrated by a rotary evaporator. The residue is diluted with 2-PrOH and stirred at room temperature for 15 min. After cooling the mixture in an ice bath, the solid is isolated by filtration and washed with 2-PrOH. The product is obtained in the form of a yellow solid, 165° C.(Dec). The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 2.39 (s, 3H), 6.23 (d, 1H), 6.86 (d, 1H), 7.19-7.4 (m, 4H).

Workup

  1. temperaturecooled in an ice bath
  2. additionare added dropwise
  3. customthe temperature below 5° C
  4. customa precipitate is formed
  5. filtrationThe precipitate is filtered off
  6. washwashed with THF
  7. concentrationThe filtrate is concentrated by a rotary evaporator
  8. additionThe residue is diluted with 2-PrOH
  9. stirringstirred at room temperature for 15 min
  10. temperatureAfter cooling the mixture in an ice bath
  11. customthe solid is isolated by filtration
  12. washwashed with 2-PrOH
  13. customThe product is obtained in the form of a yellow solid, 165° C.(Dec)

Sources & evidence

ORD record
ord-28300f629c8544ac8209bef1d4b49792
Source dataset
uspto-grants-2002_11
Patent number
US06485886B1

Reaction notes

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