Tetrahydrofuran → HCID 85317206, compound

HRID 1657192Notes

Reaction equation

HRID 1657192 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([NH:10][CH3:11])=[CH:7][C:8]#[N:9])=[CH:4][CH:3]=1.[Br:14]Br.O1CCCC1>C(Cl)(Cl)(Cl)Cl>[Br:14][C:7](=[C:6]([NH:10][CH3:11])[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:13][CH:12]=1)[C:8]#[N:9]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24408Bromine2×HCID 67753963HCID 67753963, compound

Product 1

HCID 85317206HCID 85317206, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of p-chloro-β-(methylamino)cinnamonitrile (19.3 g, 0.1 mol) in carbon tetrachloride at 70° C. is treated dropwise with a solution of bromine (16.8 g, 0.105 mol) in carbon tetrachloride over a 30-40 minute period (tetrahydrofuran is added as needed during the bromine addition to aid dissolution of the reaction mixture). The reaction mixture is stirred for 30 minutes at 70° C., cooled to room temperature and concentrated to give a yellow crystalline precipitate. The mixture is filtered, the filter cake is washed with carbon tetrachloride and dried to give the title product as a yellow solid, 18.8 g (69% yield), mp 178.0°-178.5° C., identified by IR, NMR and mass spectral analyses.

Workup

  1. additionis added
  2. dissolutiondissolution of the reaction mixture)
  3. temperaturecooled to room temperature
  4. concentrationconcentrated
  5. customto give a yellow crystalline precipitate
  6. filtrationThe mixture is filtered
  7. washthe filter cake is washed with carbon tetrachloride
  8. customdried

Sources & evidence

ORD record
ord-1011f82c72434ea684181eb3fe02a6e7
Source dataset
uspto-grants-1993_10
Patent number
US05256796

Reaction notes

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