3-(Trifluoromethyl)benzaldehyde → N*3*-(3,5-Dichloro-phenyl)-N*5*-(3-trifluoromethyl-benzyl)-1H-[1,2,4]triazole-3,5-diamine

HRID 1486590Notes

Reaction equation

HRID 1486590 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([NH2:15])[NH:12][N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.ClC1C=C(N=C=S)C=C(Cl)C=1C#N.[F:29][C:30]([F:40])([F:39])[C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=1)[CH:34]=O.[BH4-].[Na+]>CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([NH:15][CH2:34][C:33]3[CH:36]=[CH:37][CH:38]=[C:31]([C:30]([F:29])([F:39])[F:40])[CH:32]=3)[NH:12][N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

7

Reactant 4

HCID 679903-(Trifluoromethyl)benzaldehydeHCID 4311764Sodium borohydrideHCID 727146143-Amino-5-(3,5-dichloroanilino)-s-triazoleHCID 867076002,6-Dichloro-4-isothiocyanatobenzonitrile

Product 1

HCID 178506159N*3*-(3,5-Dichloro-phenyl)-N*5*-(3-trifluoromethyl-benzyl)-1H-[1,2,4]triazole-3,5-diamineYield 46%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of N3-(3,5-dichlorophenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 2 (80 mg, 0.33 mmol) in 5 mL methanol, was added 3-(trifluoromethyl)benzaldehyde (114 mg, 0.66 mmol). The reaction mixture was stirred overnight, after which, sodium borohydride (24.8 mg, 0.656 mmol) was added and the mixture was for stirred for 10 min. The reaction was diluted the water (20 mL) and extracted with EtOAc (3×10 mL). The organic layers were combined and dried with sodium sulfate. The solvent was removed and the residue was chromatographed on a combiflash machine (6% methanol/methylene chloride) to give 61 mg (46%) of the desired product. MS +m/z: 401.9 (M+H)+

Workup

  1. stirringfor stirred for 10 min
  2. extractionextracted with EtOAc (3×10 mL)
  3. dry with materialdried with sodium sulfate
  4. customThe solvent was removed
  5. customthe residue was chromatographed on a combiflash machine (6% methanol/methylene chloride)

Sources & evidence

ORD record
ord-9aa7630a2cf248acb1e0611c9635ae49
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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