Water → HCID 20330244, compound

HRID 2057750Notes

Reaction equation

HRID 2057750 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([C:9]1[O:10][C:11]([C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[CH:15]=2)=[N:12][N:13]=1)(=O)[NH2:7].O>N1C=CC=CC=1>[C:6]([C:9]1[O:10][C:11]([C:14]2[CH:15]=[C:16]([CH3:21])[CH:17]=[C:18]([CH3:20])[CH:19]=2)=[N:12][N:13]=1)#[N:7]

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 20330242HCID 20330242, compound

Product 1

HCID 20330244HCID 20330244, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

200 g of phosphorus oxychloride are added to a suspension of 189.5 g of 2-carbamoyl-5-(3,5-dimethylphenyl)-1,3,4-oxadiazole in 873 cm3 of anhydrous pyridine, in the course of one hour and whilst stirring. During this addition, the temperature of the reaction medium rises from 20° to 42° C. The stirring is continued for 4 hours, whilst allowing the temperature of the medium to return to 20° C. The reaction mixture is then poured into 8.7 liters of water and the precipitate which forms is filtered off, washed twice with 500 cm3 of water and then dried in the air. After recrystallization from isopropanol, 163 g of solid 2-cyano-5-(3,5-dimethylphenyl)-1,3,4-oxadiazole, which melts at 127° C., are obtained.

Workup

  1. additionDuring this addition
  2. customrises from 20° to 42° C
  3. customto return to 20° C
  4. filtrationthe precipitate which forms is filtered off
  5. washwashed twice with 500 cm3 of water
  6. customdried in the air
  7. customAfter recrystallization from isopropanol, 163 g of solid 2-cyano-5-(3,5-dimethylphenyl)-1,3,4-oxadiazole, which melts at 127° C.
  8. customare obtained

Sources & evidence

ORD record
ord-03604d64119d4c7ca6aaf124f8f68616
Source dataset
uspto-grants-1980_07
Patent number
US04212867

Reaction notes

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