Acetic Acid → HCID 178486138, compound

HRID 1486577Notes

Reaction equation

HRID 1486577 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:23]=[CH:22][C:21]([S:24]([N:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])=[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:23]=[CH:22][C:21]([S:24]([N:27]([CH3:28])[CH3:29])(=[O:26])=[O:25])=[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 20497477HCID 20497477, compoundHCID 727146143-Amino-5-(3,5-dichloroanilino)-s-triazole

Product 1

HCID 178486138HCID 178486138, compoundYield 66%

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 (5 mL) was added 4-formyl-N,N-dimethyl-benzenesulfonamide (96.1 mg, 451 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 (65.7 mg, 615 μmol) was added and the stirring was continued for 5 days. The reaction mixture was poured into 0.1N HCl solution (25 ml) to give a suspension, and the suspension was filtered to give an off white solid as desired product (119 mg, 66% yield). MS +m/z: 441 (M+H)+

Workup

  1. addition2-picoline borane complex (65.7 mg, 615 μmol) was added
  2. waitthe stirring was continued for 5 days
  3. customto give a suspension
  4. filtrationthe suspension was filtered

Sources & evidence

ORD record
ord-2fb91ba1b0e84d7d8b584dcc0b49f782
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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