Toluene → HCID 86739161, compound

HRID 905366Notes

Reaction equation

HRID 905366 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([Br:9])[C:6]([OH:10])=[C:5]([Br:11])[CH:4]=1)#[N:2].C1(C)C=CC=CC=1.C(N(CC)CC)C.[Cl:26][CH:27]([O:31][N:32]=[CH:33][C:34]1[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28](Cl)=[O:29]>CCCCCCC.C(O)(C)C>[Cl:26][CH:27]([O:31][N:32]=[CH:33][C:34]1[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]([O:10][C:6]1[C:5]([Br:11])=[CH:4][C:3]([C:1]#[N:2])=[CH:8][C:7]=1[Br:9])=[O:29]

Participants

7

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 15531BromoxynilHCID 86739160HCID 86739160, compound

Product 1

HCID 86739161HCID 86739161, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8900HeptaneSolvent

Procedure

A mixture of 2.1 gm. (0.0076 mole) of 4-cyano-2,6-dibromophenol (m.p. 190.0°-191.5° C.), 40 ml. of toluene and 0.8 gm. (0.008 mole) of triethylamine was stirred in a system protected from atmospheric moisture by a `drying tube`, and to it there were added, in portions, a total of 2.0 grams (0.0075 mole) of 2,6-dichlorobenzylideneaminooxyacetyl chloride. The reaction mixture was then heated for an hour on the steambath; it was filtered hot, washing the triethylamine hydrochloride on the filter with hot toluene, then discarding it. The combined filtrates were evaporated to dryness under reduced pressure, and the residue was triturated with cold methanol, then filtered. The filter-cake was then washed with cold methanol and air-dried to obtain 3.3 gm. (85.6%) of colorless solid, m.p. 166°-168° C. This material was treated with boiling isopropyl alcohol and n-heptane mixture, and was then cooled in ice bath. The solid present was removed by filration, washed on the filter with n-hexane and dried in air to obtain 3.1 gm. of crystalline product melting at 168.0°-170.5° C. (uncorrected).

Workup

  1. additionA mixture of 2.1 gm
  2. customdrying tube`, and to it there
  3. additionwere added, in portions
  4. temperatureThe reaction mixture was then heated for an hour on the steambath
  5. filtrationit was filtered hot
  6. washwashing the triethylamine hydrochloride on the
  7. filtrationfilter with hot toluene
  8. customThe combined filtrates were evaporated to dryness under reduced pressure
  9. customthe residue was triturated with cold methanol
  10. filtrationfiltered
  11. washThe filter-cake was then washed with cold methanol
  12. customair-dried
  13. customto obtain 3.3 gm
  14. temperaturewas then cooled in ice bath
  15. customThe solid present was removed by filration
  16. washwashed on the
  17. filtrationfilter with n-hexane
  18. customdried in air
  19. customto obtain 3.1 gm

Sources & evidence

ORD record
ord-de2deb13900c4e79b3bd23ad5675b90a
Source dataset
uspto-grants-1983_12
Patent number
US04423241

Reaction notes

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