Hydrazine → 4-(5-amino-1H-1,2,4-triazol-3-ylamino)-2,6-dichlorobenzonitrile

HRID 1486585Notes

Reaction equation

HRID 1486585 reaction equation
[C:1](/[N:3]=[C:4](\SC)/[NH:5][C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([C:13]#[N:14])=[C:8]([Cl:15])[CH:7]=1)#[N:2].[NH2:18][NH2:19]>C(O)C>[NH2:2][C:1]1[NH:19][N:18]=[C:4]([NH:5][C:6]2[CH:11]=[C:10]([Cl:12])[C:9]([C:13]#[N:14])=[C:8]([Cl:15])[CH:7]=2)[N:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 178503893(Z)-methyl N'-cyano-N-(3,5-dichloro-4-cyanophenyl)carbamimidothioate

Product 1

HCID 727067564-(5-amino-1H-1,2,4-triazol-3-ylamino)-2,6-dichlorobenzonitrileYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (Z)-methyl N′-cyano-N-(3,5-dichloro-4-cyanophenyl)carbamimidothioate (234 mg, 821 μmol, Eq: 1.00) and hydrazine (263 mg, 258 μl, 8.21 mmol, Eq: 10) in ethanol (10 mL) was heated at 65° C. o/n. The reaction mixture was concentrated and chromatographed (23 Supelco, 100% DCM to 5% to 10% MeOH/DCM to give 156 mg (71%) of desired product as an off-white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customchromatographed (23 Supelco, 100% DCM to 5% to 10% MeOH/DCM

Sources & evidence

ORD record
ord-db21468bb2414658aee4eaee8cc833e1
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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