Acetic Acid → HCID 178509836, compound

HRID 1486576Notes

Reaction equation

HRID 1486576 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.[CH:16]([C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1)=O.C(O)(=O)C.Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([NH:15][CH2:16][C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=3)[NH:12][N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 660424-CyanobenzaldehydeHCID 727146143-Amino-5-(3,5-dichloroanilino)-s-triazole

Product 1

HCID 178509836HCID 178509836, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N3-(3,5-dichlorophenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 2 (100 mg, 410 μmol) in MeOH (3.5 mL) was added 4-formylbenzonitrile (53.7 mg, 410 μmol) followed by acetic acid (36.7 mg, 35 μl, 611 μmol). The reaction was stirred at room temperature for 15 minutes, 2-picoline borane complex (52.6 mg, 492 μmol) was added and the stirring was continued overnight. The reaction mixture was poured into 0.1N HCl solution (25 ml). The volume was reduced and the resulting suspension was filtered to give an off white solid as desired product (109 mg, 67% yield). MS +m/z: 358 (M+H)+

Workup

  1. addition2-picoline borane complex (52.6 mg, 492 μmol) was added
  2. waitthe stirring was continued overnight
  3. filtrationthe resulting suspension was filtered

Sources & evidence

ORD record
ord-d0ca830a04a54fe895607e9bc8aa4495
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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