Triethylamine → HCID 10883497, compound

HRID 849276Notes

Reaction equation

HRID 849276 reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][N:4]=[C:5](Cl)[C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[CH:7]=1.Cl[C:18](=[CH2:21])[C:19]#[N:20].C(N(CC)CC)C.[Br:29]Br>CN(C)C=O.O.CCCCCCC.C(OCC)(=O)C>[Br:29][C:21]1[C:18]([C:19]#[N:20])=[C:5]([C:6]2[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[CH:7]=2)[NH:4][C:3]=1[C:2]([F:16])([F:15])[F:1]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 24408BromineHCID 701982-ChloroacrylonitrileHCID 11087554HCID 11087554, compound

Product 1

HCID 10883497HCID 10883497, compoundYield 46.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Procedure

A solution of N-(2,2,2-trifluoroethyl)-3,5-dichlorobenzimidoyl chloride (8.72 g, 0.03 mol) in N,N-dimethylformamide is treated with 2-chloroacrylonitrile (3.0 g, 0.0345 mol) under a nitrogen atmosphere. Triethylamine (9.56 g, 0.0945 mol) is added slowly at 50° C. over two hours and the reaction mixture is stirred at 58°-60° C. for 18 hours. Bromine (4.8 g, 0.03 mol) is then added over 20 minutes as the temperature rises from 25° C. to 36° C. The resultant reaction mixture is diluted with water and extracted with methylene chloride. Evaporation and flash column chromatography using silica gel and a 20% ethyl acetate in heptane solution gives the title product as a white crystalline solid (5.4 g, 46.9% yield) which is identified by 19F and 1H NMR.

Workup

  1. customrises from 25° C. to 36° C
  2. customThe resultant reaction mixture
  3. extractionextracted with methylene chloride
  4. customEvaporation and flash column chromatography

Sources & evidence

ORD record
ord-24cf429f6ba74c7dba567db0370481df
Source dataset
uspto-grants-2000_01
Patent number
US06011161

Reaction notes

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