Methanol → 3-[4-(1H-Benzoimidazol-2-yl)-furazan-3-ylamino]-propionitrile

HRID 132002Notes

Reaction equation

HRID 132002 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:15])=[N:12][O:13][N:14]=1.CO.[C:18](#[N:21])[CH:19]=[CH2:20]>N1C=CC=CC=1>[NH:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[C:2]1[C:10]1[C:11]([NH:15][CH2:20][CH2:19][C:18]#[N:21])=[N:12][O:13][N:14]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 7855AcrylonitrileHCID 7385314-(1H-benzimidazol-2-yl)-1,2,5-oxadiazol-3-amine

Product 1

HCID 1363893133-[4-(1H-Benzoimidazol-2-yl)-furazan-3-ylamino]-propionitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-(1H-benzimidazol-2-yl)-furazan-3-ylamine (0.10 g, 0.497 mmol) in pyridine (5 ml) sodium in methanol (0.02 g, 0.86 mmol in 1 ml) and acrylonitrile (0.03 g, 0.39 mmol) are added sequentially at 0° C. The mixture is stirred over night. Evaporation of the solvent under reduced pressure and partitioning of the resulting residue between water and ethyl acetate followed by drying of the organic solution over sodium sulphate gives the title compound in pure form. 1H-NMR (400 MHz, d6-DMSO): 13.7 (s, 1H); 7.82 (d, 1H); 7.60 (d, 1H); 7.36 (m, 2H); 7.20 (t, 1H); 3.67 (q, 2H); 2.94 (t, 2H).

Workup

  1. customEvaporation of the solvent under reduced pressure
  2. custompartitioning of the resulting residue between water and ethyl acetate
  3. dry with materialby drying of the organic solution over sodium sulphate

Sources & evidence

ORD record
ord-99e13acc339c47ae8677c3ab58efdb21
Source dataset
uspto-grants-2008_06
Patent number
US07385061B2

Reaction notes

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