O-Phenylenediamine → Thiabendazole

HRID 1033528

Reaction equation

HRID 1033528 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9]([C:11]1[N:12]=[CH:13][S:14][CH:15]=1)#N>O>[CH:4]1[CH:5]=[CH:6][C:1]2[N:8]=[C:9]([C:11]3[N:12]=[CH:13][S:14][CH:15]=3)[NH:7][C:2]=2[CH:3]=1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 150694-Cyanothiazole

Product 1

HCID 5430ThiabendazoleYield 89.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

The product, thiabendazole, precipitated as it was formed in the reaction mixture. The reaction was monitored by gas chromatography and determined to be complete when the peaks corresponding to o-phenylenediamine and 4-cyanothiazole were negligible. The reaction mass was allowed to cool to 50° C. and 150 ml of 50° C. deionized water was added to thin the mixture before being vacuum filtered using a medium fritted glass filter. The solid product was washed four times with 300 ml portions of deionized water. The washed precipitate was dried overnight in a vacuum oven under 15-20" Hg and at a temperature of 80°-90° C. A total of 89.77 grams of thiabendazole were obtained which corresponds to an 89.3% yield. The color of dry thiabendazole was cream. High Performance Liquid Chromatography (HPLC) using a Hewlett-Packard Model 1090M showed that the purity was 98.77% (based on % area).

Workup

  1. customThe product, thiabendazole, precipitated as it
  2. customwas formed in the reaction mixture
  3. custom150 ml of 50° C.
  4. additionwas added
  5. filtrationfiltered
  6. filtrationfilter
  7. washThe solid product was washed four times with 300 ml portions of deionized water
  8. customThe washed precipitate was dried overnight in a vacuum oven under 15-20" Hg and at a temperature of 80°-90° C

Sources & evidence

ORD record
ord-1942a8dab9ce4763b2b90060eddba93b
Source dataset
uspto-grants-1994_05
Patent number
US05310924

Linked notes

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