2-(Benzyloxy)-3,5-dibromobenzaldehyde → HCID 178512744, compound

HRID 597721Notes

Reaction equation

HRID 597721 reaction equation
Cl.[NH2:2][NH:3][C:4]([NH:6][NH2:7])=[NH:5].[CH2:8]([O:15][C:16]1[C:23]([Br:24])=[CH:22][C:21]([Br:25])=[CH:20][C:17]=1[CH:18]=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[H][H]>Cl>[Br:24][C:23]1[C:16]([O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:17]([CH:20]=[C:21]([Br:25])[CH:22]=1)[CH:18]=[N:2][NH:3][C:4]([NH:6][N:7]=[CH:18][C:17]1[CH:20]=[C:21]([Br:25])[CH:22]=[C:23]([Br:24])[C:16]=1[O:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[NH:5]

Participants

5

Reactant 3

HCID 14943372-(Benzyloxy)-3,5-dibromobenzaldehydeHCID 178418361HCID 178418361, compoundHCID 178479531HCID 178479531, compound

Product 1

HCID 178512744HCID 178512744, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a mixture of 2.1 grams (0.015 mole) of N,N'-diaminoguanidine, hydrochloride in 50 milliliters of 2B-ethanol and 2.0 milliliters of concentrated hydrochloric acid was added 11.1 grams (0.03 mole) of 2-benzyloxy-3,5-dibromobenzaldehyde. The mixture was stirred and heated to reflux temperature and maintained at this temperature overnight. At the completion of the reaction, the insoluble crystals contained in the reaction mixture were removed by filtration and dried under reduced pressure. The solid crude 1,3-bis[((3,5-dibromo-2-benzyloxybenzylidene)-amino]guanidine, hydrochloride product was mixed with 250 milliliters of benzene refluxed, recovered by filtration and dried. The product was obtained in a yield of 11.3 grams and melted at 217°-218° C. Upon analysis, the product was found to have carbon, hydrogen and nitrogen contents of 41.83, 3.00 and 8.48 percent, respectively, as compared with the theoretical contents of 41.98, 2.92 and 8.44 percent, respectively, calculated for the abovenamed structure.

Workup

  1. temperatureheated
  2. temperatureto reflux temperature
  3. temperaturemaintained at this temperature overnight
  4. customAt the completion of the reaction
  5. customwere removed by filtration
  6. customdried under reduced pressure
  7. additionThe solid crude 1,3-bis[((3,5-dibromo-2-benzyloxybenzylidene)-amino]guanidine, hydrochloride product was mixed with 250 milliliters of benzene
  8. temperaturerefluxed
  9. filtrationrecovered by filtration
  10. customdried
  11. customThe product was obtained in a yield of 11.3 grams and melted at 217°-218° C

Sources & evidence

ORD record
ord-fde0dd452c434535aee026afdb908733
Source dataset
uspto-grants-1977_03
Patent number
US04015016

Reaction notes

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