Hydrochloric Acid → HCID 20530932, compound

HRID 1759498Notes

Reaction equation

HRID 1759498 reaction equation
[Cl-].[C:2]1([N+:8]#[N:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10](#[N:14])[CH2:11][C:12]#[N:13].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.Cl.[N:27]1C=CC=CC=1>>[C:2]1([N:8]2[N:27]=[C:11]([C:12]#[N:13])[C:10]([NH2:14])=[N:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 8010MalononitrileHCID 60992Benzenediazonium chloride

Product 1

HCID 20530932HCID 20530932, compound

Procedure

20 Parts phenylazo-malonic dinitrile prepared by coupling phenyldiazonium chloride with malononitrile and 12.5 parts hydroxylaminochlorohydrate are suspended in 100 parts pyridine. 33.7 parts para-toluenesulfonic acid chloride are added thereto with ice cooling and stirred at room temperature from 5 hours. Then the mixture is adjusted with concentrated hydrochloric acid, extracted with 100 parts methylene chloride and the organic phase dried with the solvent being separated by distillation. The aminotriazole product is recrystallized from a methanol/water mixture.

Workup

  1. custom20 Parts phenylazo-malonic dinitrile prepared
  2. extractionextracted with 100 parts methylene chloride
  3. customthe organic phase dried with the solvent
  4. custombeing separated by distillation
  5. customThe aminotriazole product is recrystallized from a methanol/water mixture

Sources & evidence

ORD record
ord-959690c0454c48dfb8f7ee0bcd7e3d7c
Source dataset
uspto-grants-1982_07
Patent number
US04341700

Reaction notes

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