Ethyl Acetate → 4-(1-(5-Hydroxymethylfur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane

HRID 637072Notes

Reaction equation

HRID 637072 reaction equation
C(OC([N:6]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[N:17]([CH2:18][C:19]3[O:20][C:21]([CH2:24][OH:25])=[CH:22][CH:23]=3)[C:16]3[CH:26]=[CH:27][CH:28]=[CH:29][C:15]=3[N:14]=2)[CH2:8][CH2:7]1)=O)C.[OH-].[Na+].C(OCC)(=O)C>C(O)(C)C>[OH:25][CH2:24][C:21]1[O:20][C:19]([CH2:18][N:17]2[C:16]3[CH:26]=[CH:27][CH:28]=[CH:29][C:15]=3[N:14]=[C:13]2[N:9]2[CH2:10][CH2:11][CH2:12][NH:6][CH2:7][CH2:8]2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 184645131-ethoxycarbonyl-4-(1-(5-hydroxymethylfur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane

Product 1

HCID 184649364-(1-(5-Hydroxymethylfur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Combine 1-ethoxycarbonyl-4-(1-(5-hydroxymethylfur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane (4 mmol) and sodium hydroxide (8 mmol) in isopropanol (20 mL). Heat to reflux. After 2 days, evaporate the reaction mixture in vacuo to give a residue. Combine the residue and ethyl acetate. Extract with water and brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. customevaporate the reaction mixture in vacuo
  3. customto give a residue
  4. extractionExtract with water and brine
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo

Sources & evidence

ORD record
ord-dc0e8e76d9ad47c4ad21740dbecddae8
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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