1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 54334327, compound

HRID 2082103Notes

Reaction equation

HRID 2082103 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([Cl:18])=[C:16]([C:19]#[N:20])[C:15]([S:21][C:22]([F:25])([F:24])[F:23])=[C:14]1[CH2:26][CH:27](Cl)[C:28]#[N:29].N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1.CCOCC>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([Cl:18])=[C:16]([C:19]#[N:20])[C:15]([S:21][C:22]([F:25])([F:24])[F:23])=[C:14]1[CH:26]=[CH:27][C:28]#[N:29]

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22418338HCID 22418338, compound

Product 1

HCID 54334327HCID 54334327, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

The 1-(2,6-dichloro-4-trifluoromethylphenyl)-2-(2-chloro-2-cyanoethyl)-3-trifluoromethylthio-4-cyano-5-chloropyrrole prepared above was dissolved in 125 mL of toluene and treated with 1.65 mL (1.68 g, 11.1 mmoles) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) at room temperature for 1 hour. The reaction mixture was then diluted with ether, washed with water, dried over anhydrous MgSO4 and concentrated to give 4.84 g (98%) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-2-(2-cyanoethenyl)-3-trifluoromethylthio-4-cyano-5-chloropyrrole as a yellow solid.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-686e0d72735f433bbba5ff5f630f24cb
Source dataset
uspto-grants-1993_02
Patent number
US05187185

Reaction notes

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