Hydrochloric Acid → HCID 178504754, compound

HRID 1486575Notes

Reaction equation

HRID 1486575 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.[CH3:16][S:17]([C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1)(=[O:19])=[O:18].Cl>CO.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([NH:15][CH2:24][C:23]3[CH:22]=[CH:21][C:20]([S:17]([CH3:16])(=[O:19])=[O:18])=[CH:27][CH:26]=3)[NH:12][N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2203764-(Methylsulfonyl)benzaldehydeHCID 727146143-Amino-5-(3,5-dichloroanilino)-s-triazole

Product 1

HCID 178504754HCID 178504754, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent3×

Procedure

To a solution of N3-(3,5-dichlorophenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 2 (200 mg, 819 μmol) in MeOH (5 mL) was added a suspension of 4-methylsulfonylbenzaldehyde (158 mg, 860 μmol) in acetic acid (75 μl) and MeOH (2 mL). The reaction was stirred at room temperature for 15 minutes, 2-picoline borane complex (140 mg, 1.31 mmol, Aldrich) was added and the stirring was continued for 3 days. The reaction mixture was diluted with MeOH (6 mL) and poured into 0.1N HCl solution (10 ml). The resulting suspension was filtered and washed with water to give an off white solid as desired product (228 mg, 67% yield). MS +m/z: 412 (M+H)+

Workup

  1. addition2-picoline borane complex (140 mg, 1.31 mmol, Aldrich) was added
  2. waitthe stirring was continued for 3 days
  3. filtrationThe resulting suspension was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-aa1695972b6543f1b51525d8c9a0a482
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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