N-(2-Cyanoethyl)-N-formylglycine → 1-(2-Cyanoethyl)-3-(2,3-dichlorophenyl)-4-trifluoromethylpyrrole

HRID 1607912Notes

Reaction equation

HRID 1607912 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]#[C:10][C:11]([F:14])([F:13])[F:12].[C:15]([CH2:17][CH2:18][N:19]([CH:24]=O)[CH2:20]C(O)=O)#[N:16]>C(OC(=O)C)(=O)C>[C:15]([CH2:17][CH2:18][N:19]1[CH:24]=[C:10]([C:11]([F:14])([F:12])[F:13])[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])=[CH:20]1)#[N:16]

Participants

4

Reactant 2

HCID 19849818N-(2-Cyanoethyl)-N-formylglycineHCID 198498191,2-Dichloro-3-(trifluoroprop-1-YN-1-YL)benzene

Product 1

HCID 198498201-(2-Cyanoethyl)-3-(2,3-dichlorophenyl)-4-trifluoromethylpyrrole

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

23.9 g of 2,3-dichloro-(3,3,3-trifluoropropyn-1-yl)-benzene and 15.6 g of N-(2-cyanoethyl)-N-formylglycine are dissolved in 100 ml of acetic anhydride, and the solution is refluxed for 24 h. The mixture is concentrated by evaporation under reduced pressure; the residue is then taken up in toluene, and purified by chromatography through silica gel. The solvent is evaporated off, and from the eluate is obtained 1-(2-cyanoethyl)-3-(2,3-dichlorophenyl)-4-trifluoromethylpyrrole, m.p. 83°-85° C. from ether/hexane (compound No. 3.28).

Workup

  1. temperaturethe solution is refluxed for 24 h
  2. concentrationThe mixture is concentrated by evaporation under reduced pressure
  3. custompurified by chromatography through silica gel
  4. customThe solvent is evaporated off

Sources & evidence

ORD record
ord-5945e11c32724a2096ab34deff8417c0
Source dataset
uspto-grants-1989_09
Patent number
US04868202

Reaction notes

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