Hydrochloric Acid → Bendazol [INN:DCF]

HRID 1383956Notes

Reaction equation

HRID 1383956 reaction equation
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1N.O>CO>[CH2:1]([C:8]1[NH:9][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7243O-PhenylenediamineHCID 8794Phenylacetonitrile

Product 1

HCID 12132Bendazol [INN:DCF]

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A 1 M solution of benzyl cyanide in anhydrous methanol was treated with hydrogen chloride gas at 0° C. for about thirty minutes. The mixture was stirred for two hours at 0° C. and then a 1 M solution of diaminobenzene was added and the resulting solution was stirred at 0° C. The progress of the reaction was monitored by thin layer chromatography. The reaction mixture was then poured into water. The unreacted nitrile was extracted with ethyl acetate. The aqueous layer was neutralized with 1 N sodium hydroxide. The organic fraction was extracted with ethyl acetate and condensed. The desired title product was recrystallized from methanol/water.

Workup

  1. stirringthe resulting solution was stirred at 0° C
  2. extractionThe unreacted nitrile was extracted with ethyl acetate
  3. extractionThe organic fraction was extracted with ethyl acetate and condensed
  4. customThe desired title product was recrystallized from methanol/water

Sources & evidence

ORD record
ord-223aa794146644aaba999122c9a326c5
Source dataset
uspto-grants-2001_07
Patent number
US06255494B1

Reaction notes

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