Hydrochloric Acid → 2-(2-Nitro-4-(methylsulfonyl)benzoyl)-2-(1-methyl-1,2,4-triazol-5-yl)acetonitrile

HRID 514172Notes

Reaction equation

HRID 514172 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].[CH3:17][N:18]1[C:22]([CH2:23][C:24]#[N:25])=[N:21][CH:20]=[N:19]1.C(N(C(C)C)CC)(C)C.Cl>CO>[N+:1]([C:4]1[CH:12]=[C:11]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([CH:23]([C:22]1[N:18]([CH3:17])[N:19]=[CH:20][N:21]=1)[C:24]#[N:25])=[O:7])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 148001864-(Methanesulfonyl)-2-nitrobenzoyl chlorideHCID 656015352-(1-methyl-1H-1,2,4-triazol-5-yl)acetonitrile

Product 1

HCID 896895552-(2-Nitro-4-(methylsulfonyl)benzoyl)-2-(1-methyl-1,2,4-triazol-5-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

263 mg (1.0 mmol) of 2-nitro-4-(methylsulfonyl)benzoyl chloride are added at 0° C. to 122 mg (1.0 mmol) of 2-(1-methyl-1,2,4-triazol-5-yl)acetonitrile and 258 mg (2 mmol) of diisopropylethylamine. The mixture is then stirred at room temperature for 16 h. 1 ml of methanol is then added and, after 15 min, 2N HCl is added. The mixture is extracted with dichloromethane, dried over Na2SO4, evaporated and purified by means of RP-HPLC (acetonitrile/water). Yield 156 mg (45%).

Workup

  1. extractionThe mixture is extracted with dichloromethane
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. custompurified by means of RP-HPLC (acetonitrile/water)

Sources & evidence

ORD record
ord-3eb6525a1e4e4ec59c3aea75ba5f89ce
Source dataset
uspto-grants-2015_08
Patent number
US09107414B2

Reaction notes

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