Triethylamine → HCID 13393815, compound

HRID 978782Notes

Reaction equation

HRID 978782 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]=1[CH:18]=[N:19]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>ClCCCl.C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:3]=1[C:18]#[N:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86146364HCID 86146364, compound

Product 1

HCID 13393815HCID 13393815, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 25.7 g 4-chloro-3-hydroxyiminomethyl-flav-3-ene and 28.3 g triphenylphosphine in 250 ml 1,2-dichloroethane and 8.7 ml carbon tetrachloride is heated at 60° C. To this solution one adds 12.54 ml triethylamine. The temperature is maintained between 62°-65° C. during the addition and for further 25 minutes. The mixture is cooled to 0° C., filtered and evaporated. The crude material is extracted with hexane. The combined extracts are evaporated and purified by column chromatography on silicagel using a mixture of dichloromethane and hexane as eluant. The pure fraction is evaporated and crystallized in diisopropylether. Pure 4-chloro-3-cyano-flav-3-ene is obtained as pale yellow crystalls; m.p. 99° C.

Workup

  1. temperatureThe temperature is maintained between 62°-65° C. during the addition and for further 25 minutes
  2. filtrationfiltered
  3. customevaporated
  4. extractionThe crude material is extracted with hexane
  5. customThe combined extracts are evaporated
  6. custompurified by column chromatography on silicagel
  7. additiona mixture of dichloromethane and hexane as eluant
  8. customThe pure fraction is evaporated
  9. customcrystallized in diisopropylether

Sources & evidence

ORD record
ord-3cf9fa8d45b845b29f3dcfdc3276bd41
Source dataset
uspto-grants-1987_05
Patent number
US04665202

Reaction notes

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