Tetrahydrofuran → HCID 85317206, compound

HRID 483628Notes

Reaction equation

HRID 483628 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:15]=[CH:14][C:7]([C:8]([NH:12][CH3:13])=[CH:9][C:10]#[N:11])=[CH:6][CH:5]=1.O1CCCC1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:9](=[C:8]([NH:12][CH3:13])[C:7]1[CH:6]=[CH:5][C:4]([Cl:3])=[CH:15][CH:14]=1)[C:10]#[N:11]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24408BromineHCID 67753963HCID 67753963, compound

Product 1

HCID 85317206HCID 85317206, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent3×

Procedure

A solution of bromine (10.9 mL, 33.6 g, 0.21 mol) in carbon tetrachloride is added to a mixture of p-chloro-β-(methylamino)cinnamonitrile, (E)- or (Z)- (38.53 g, 0.2 mol) in carbon tetrachloride and tetrahydrofuran at 55°-60° C. over 30 minutes. The reaction mixture is cooled to room temperature, concentrated in vacuo to one-half of the original volume and filtered to obtain a solid. The solid is diluted with carbon tetrachloride and the resulting mixture is heated at reflux, cooled and filtered to give the title product as a yellow solid (43.6 g, mp 178°-178.5° C.) which is identified by 1H and 13CNMR spectral analyses.

Workup

  1. concentrationconcentrated in vacuo to one-half of the original volume
  2. filtrationfiltered
  3. customto obtain a solid
  4. temperaturethe resulting mixture is heated
  5. temperatureat reflux
  6. temperaturecooled
  7. filtrationfiltered

Sources & evidence

ORD record
ord-6821d1b6469c45ceae189bff59288397
Source dataset
uspto-grants-1993_07
Patent number
US05225568

Reaction notes

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