Water → 2-methyl-5-cyanothio-11H-1,2,4-triazolo[2,3-c][1,3]benzodiazepine

HRID 1982140Notes

Reaction equation

HRID 1982140 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:8][N:7]=[C:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:16]=[C:17]=[S:18])[N:5]=1.[N:19]#[C:20]Br.O>O1CCCC1>[CH3:3][C:4]1[N:5]=[C:6]2[CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:16]=[C:17]([S:18][C:20]#[N:19])[N:7]2[N:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 24758Sodium hydrideHCID 233173365-Methyl-3-(o-isothiocyanatobenzyl)-1,2,4-triazole

Product 1

HCID 233173522-methyl-5-cyanothio-11H-1,2,4-triazolo[2,3-c][1,3]benzodiazepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 0.91 g of sodium hydride in 27 ml of tetrahydrofuran is added dropwise a solution of 8.74 g of 5-methyl-3-(o-isothiocyanatobenzyl)-1,2,4-triazole in 60 ml of tetrahydrofuran over a period of 20 minutes. The mixture is stirred at room temperature for 2 hours. To the resulting suspension a solution of 4.02 g of cyanogen bromide in 35 ml of tetrahydrofuran is added dropwise at 0° over a period of 15 minutes. The mixture is stirred at 0° for 1.5 hours, poured into water and extracted three times with ethyl acetate. The organic extracts are dried over magnesium sulfate, decolorized with charcoal and evaporated to give 2-methyl-5-cyanothio-11H-1,2,4-triazolo[2,3-c][1,3]benzodiazepine; IR 2150 cm-1.

Workup

  1. stirringThe mixture is stirred at 0° for 1.5 hours
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe organic extracts are dried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-f93931fb8f264d11bb2f934f58420104
Source dataset
uspto-grants-1986_06
Patent number
US04595535

Reaction notes

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