Dimethylformamide → 5-Amino-3-[(dimethylaminomethylidene)amino]-1-[methylamino(thiocarbonyl)]-1H-1,2,4-triazole

HRID 1289777Notes

Reaction equation

HRID 1289777 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([NH2:7])[N:4]([C:8]([NH:10][CH3:11])=[S:9])[N:3]=1.[CH3:12][N:13]([CH3:16])[CH:14]=O.C(N(CC)CC)C.C(Cl)(=O)C1C=CC=CC=1>O>[NH2:7][C:5]1[N:4]([C:8]([NH:10][CH3:11])=[S:9])[N:3]=[C:2]([N:1]=[CH:12][N:13]([CH3:16])[CH3:14])[N:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 10725863HCID 10725863, compound

Product 1

HCID 867525445-Amino-3-[(dimethylaminomethylidene)amino]-1-[methylamino(thiocarbonyl)]-1H-1,2,4-triazoleYield 27%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the compound (1.00 g) obtained in Example 31, dimethylformamide (25 ml) and triethylamine (1.0 ml, 7.2 mmol) was cooled to 0° C. and benzoyl chloride (0.70 ml) was gradually added dropwise thereto. The mixture was stirred at 0° C.-room temperature for 4.5 hours and the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure. After the concentration, silica gel column chromatography (chloroform-methanol) and recrystallization from chloroform-methanol gave 350 mg of pale-yellow crystals (yield 27%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled away under reduced pressure
  5. concentrationAfter the concentration, silica gel column chromatography (chloroform-methanol) and recrystallization from chloroform-methanol

Sources & evidence

ORD record
ord-e1cb432d9a5243da96f4623583cd1305
Source dataset
uspto-grants-1998_05
Patent number
US05750545

Reaction notes

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