Triethylamine → HCID 10892080, compound

HRID 1885747Notes

Reaction equation

HRID 1885747 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[CH2:5][N:6]=[C:7](Cl)[C:8]([F:11])([F:10])[F:9].Cl[C:18](=[CH2:21])[C:19]#[N:20].C(N(CC)CC)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[NH:6][C:7]([C:8]([F:11])([F:10])[F:9])=[CH:21][C:18]=2[C:19]#[N:20])[CH:13]=[CH:14][C:15]=1[Cl:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 701982-ChloroacrylonitrileHCID 10870020HCID 10870020, compound

Product 1

HCID 10892080HCID 10892080, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-(3,4-dichlorobenzyl)-2,2,2-trifluoroacetimidoyl chloride (20.0 g, 0.069 mol) and 2-chloroacrylonitrile (7.2 g, 0.082 mol) in N,N-dimethylformamide is cooled to 5° C. and treated with a solution of triethylamine (22 mL, 0.16 mol) in N,N-dimethylformamide (38 mL). When the addition is half complete, the cooling bath is removed and the reaction mixture is treated with the remaining triethylamine solution, stirred for two hours and diluted with water. The aqueous mixture is filtered to obtain the title product as a tan solid (18.38 g, mp 230°-232° C.).

Workup

  1. additionWhen the addition
  2. customthe cooling bath is removed
  3. additionthe reaction mixture is treated with the remaining triethylamine solution
  4. additiondiluted with water
  5. filtrationThe aqueous mixture is filtered

Sources & evidence

ORD record
ord-af1e57a2cf4142f390415fde9510e75d
Source dataset
uspto-grants-1992_09
Patent number
US05145986

Reaction notes

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