Dimethylformamide → HCID 86666633, compound

HRID 587848Notes

Reaction equation

HRID 587848 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1I)[C:5]([NH:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([C:15]([F:24])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])=[CH:10][C:9]=1[Cl:25])=[O:6].[CH3:30][N:31](C)C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[C:30]#[N:31])[C:5]([NH:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([C:15]([F:24])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])=[CH:10][C:9]=1[Cl:25])=[O:6]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 86666634HCID 86666634, compound

Product 1

HCID 86666633HCID 86666633, compoundYield 68.2%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

3-Chloro-N-[2,6-dichloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-4-iodobenzamide (1.59 g) was dissolved in N,N-dimethylformamide (20 ml). The resulting solution was deaerated under argon atmosphere, and then zinc cyanide (0.38 g) and tetrakis(triphenyl phosphine) palladium (0) (0.37 g) were added thereto. The mixture was heated and stirred for 7 hours at 80° C. under argon atmosphere. The reaction mixture was cooled, diluted with ethyl acetate, and then washed twice with water. The organic phase was dried over magnesium sulfate. The drying agent was removed by filtration, and the solvent was distilled off under reduced pressure to obtain a crude product, which was then purified by column chromatography to give 3-chloro-4-cyano-N-[2,6-dichloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-phenyl]-benzamide (0.90 g, yield 68.2%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureThe reaction mixture was cooled
  3. washwashed twice with water
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. customThe drying agent was removed by filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto obtain a crude product, which
  8. customwas then purified by column chromatography

Sources & evidence

ORD record
ord-e556a15e8c224110b35853361facbb8a
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

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