Phenacyl bromide → HCID 11393000, compound

HRID 553334Notes

Reaction equation

HRID 553334 reaction equation
[CH2:1](Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[NH:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[C:20]1[C:21]([NH2:25])=[N:22][O:23][N:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([N:13]1[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:11]=[C:12]1[C:20]1[C:21]([NH2:25])=[N:22][O:23][N:24]=1)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

6

Reactant 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 7385314-(1H-benzimidazol-2-yl)-1,2,5-oxadiazol-3-amine

Product 1

HCID 11393000HCID 11393000, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Phenacylbromid (0.1 g, 0.49 mmol) is added to an efficiently stirred suspension of 4-(1H-benzimidazol-2-yl)-furazan-3-ylamine (0.1 g, 0.4 mmol) [A. V. Sergievskii, O. A. Krasnoshek, S. F. Mel'nikova, I. V. Tselinskii, Russian Journal of Organic Chemistry, 2002, 38, 915-917] and potassium carbonate (0.172 g, 1.24 mmol) in dry DMF (5 ml) at room temperature. After 4 hours the reaction mixture is diluted with ethyl acetate and the organic phase is washed repeatedly with brine. Drying of the solvent, filtering and evaporation of the solvent under reduced pressure gives the title compound in crude form. The title compound is obtained in pure form by chromatography over silicagel, m.p. 202-204° C.

Workup

  1. customat room temperature
  2. washthe organic phase is washed repeatedly with brine
  3. customDrying of the solvent
  4. filtrationfiltering
  5. customevaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-3183b4f3c424424c9aae9d495ef6789c
Source dataset
uspto-grants-2011_11
Patent number
USRE042890E1

Reaction notes

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