Diethyl Ether → HCID 13067091, compound

HRID 1903625Notes

Reaction equation

HRID 1903625 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[CH:13]=[CH:14][C:15]#[N:16])=[O:5].S([CH:31]([N+:33]#[C-])C)(C1C=CC(C)=CC=1)(=O)=O.[H-].[Na+].[CH3:37][CH2:38]OCC>CS(C)=O.O.Cl>[Cl:12][C:10]1[CH:9]=[CH:8][C:7]([C:13]2[C:14]([C:31]#[N:33])=[CH:15][NH:16][C:37]=2[CH3:38])=[C:6]([C:4](=[O:5])[C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=2[Cl:1])[CH:11]=1

Participants

8

Reactant 4

HCID 3283Diethyl Ether2×HCID 24758Sodium hydrideHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzeneHCID 537352183-[4-Chloro-2-(2-chlorobenzoyl)phenyl]prop-2-enenitrile

Product 1

HCID 13067091HCID 13067091, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 33.9 g (0.11 mol) of 3-[2-(2-chlorobenzoyl)-4-chlorophenyl]-2-propenenitrile, 20 g (0.96 mol) of 1-tosylethyl isocyanide in 150 ml of dimethyl sulfoxide and 100 ml of ether was added dropwise to a suspension of 4.6 g (0.1 mol) of a 50% mineral oil dispension of sodium hydride in 100 ml of ether which was immersed in a room temperature water bath. Stirring at room temperature was continued for 2 hours. The mixture was diluted with 1.2 liters of water and 40 ml of 1 N hydrochloric acid and extracted with methylene chloride. The methylene chloride solution was washed with water, dried over anhydrous sodium sulfate and concentrated at reduced pressure to give a dark green oil. Crystallization from a mixture of ether and petroleum ether gave 4-[4-chloro-2-(2-chlorobenzoyl)phenyl]-5-methyl-1H-pyrrole-3-carbonitrile, mp 206°-208° C., as tan crystals. Recrystallization from ether gave the desired product as colorless crystals, mp 210°-211° C.

Workup

  1. customwas immersed in a room temperature
  2. extractionextracted with methylene chloride
  3. washThe methylene chloride solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated at reduced pressure
  6. customto give a dark green oil
  7. customCrystallization
  8. additionfrom a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-06f7cdc75247415681109a1bab991d1b
Source dataset
uspto-grants-1984_03
Patent number
US04436662

Reaction notes

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