Ethanol → HCID 136058090, compound

HRID 2077056Notes

Reaction equation

HRID 2077056 reaction equation
C(O)C.[Na].[C:5]1([CH2:11][C:12](=[NH:14])[NH2:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:15]([N:22]1[CH2:28][CH2:27][C:26](=O)[CH:25]([C:30](OCC)=[O:31])[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[CH2:11]([C:12]1[NH:14][C:30](=[O:31])[C:25]2[CH2:24][CH2:23][N:22]([CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:28][CH2:27][C:26]=2[N:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 27787BenzeneethanimidamideHCID 5360545Sodium2×HCID 12485292Ethyl 1-benzyl-5-oxoazepane-4-carboxylate

Product 1

HCID 136058090HCID 136058090, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethanol (50 ml) was cooled in an ice bath then sodium (442 mg, 19.2 mmol) added, with vigorous stirring. Once the sodium was dissolved, 2-phenylethanimidamide (1.29 g, 9.6 mmol) and ethyl 1-benzyl-5-oxoazepane-4-carboxylate (2.5 g, 8 mmol) was added. The reaction mixture was refluxed, under nitrogen, for 17 h. Water (10 ml) was added to quench the reaction then the reaction mixture concentrated in vacuo. The residue was partitioned between ethyl acetate (200 ml) and water (200 ml). The organic phase was dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with DCM:MeOH (98:2 to 95:5), to afford a white solid, 1.35 g, 49%

Workup

  1. temperatureThe reaction mixture was refluxed, under nitrogen, for 17 h
  2. customto quench
  3. customthe reaction
  4. concentrationthe reaction mixture concentrated in vacuo
  5. customThe residue was partitioned between ethyl acetate (200 ml) and water (200 ml)
  6. dry with materialThe organic phase was dried over magnesium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on silica gel
  9. washeluting with DCM:MeOH (98:2 to 95:5)
  10. customto afford a white solid, 1.35 g, 49%

Sources & evidence

ORD record
ord-667df14541c64531b15111c49d0dede2
Source dataset
uspto-grants-2011_04
Patent number
US07928099B2

Reaction notes

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