Diiodomethane → 4-[1-(4-Fluorophenoxymethyl)-1H-benzimidazol-2-yl]-furazan-3-ylamine

HRID 132004Notes

Reaction equation

HRID 132004 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.[C:16](=[O:19])([O-])[O-].[K+].[K+].[F:22][C:23]1[CH:28]=[CH:27][C:26](O)=[CH:25][CH:24]=1.ICI>>[F:22][C:23]1[CH:28]=[CH:27][C:26]([O:19][CH2:16][N:3]2[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=[C:2]2[C:10]2[C:11]([NH2:15])=[N:12][O:13][N:14]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 4

HCID 6346DiiodomethaneHCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 7385314-(1H-benzimidazol-2-yl)-1,2,5-oxadiazol-3-amine

Product 1

HCID 674581694-[1-(4-Fluorophenoxymethyl)-1H-benzimidazol-2-yl]-furazan-3-ylamine

Procedure

To a solution of 4-(1H-benzimidazol-2-yl)-furazan-3-ylamine (0.10 g, 0.497 mmol) is added potassium carbonate (0.172 g, 1.24 mmol) followed by 4-fluorophenol (0.0557 g, 0.497 mmol) and diiodomethane (0.133 g, 0.497 mmol). 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 and chromatography of the residue gives the title compound as a colorless solid, m.p. 155-158° C.

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 and chromatography of the residue

Sources & evidence

ORD record
ord-4ee40691d57146eea138828ba17bbfdf
Source dataset
uspto-grants-2008_06
Patent number
US07385061B2

Reaction notes

Loading…