Ethanol → HCID 136058092, compound

HRID 2077052Notes

Reaction equation

HRID 2077052 reaction equation
C(O)C.[Na].[Cl:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13](=[NH:15])[NH2:14])[CH:9]=[CH:10][CH:11]=1.[CH2:16]([N:23]1[CH2:29][CH2:28][C:27](=O)[CH:26]([C:31](OCC)=[O:32])[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O>[CH2:16]([N:23]1[CH2:24][CH2:25][C:26]2[C:31](=[O:32])[NH:15][C:13]([CH2:12][C:8]3[CH:9]=[CH:10][CH:11]=[C:6]([Cl:5])[CH:7]=3)=[N:14][C:27]=2[CH2:28][CH2:29]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 5360545Sodium2×HCID 12485292Ethyl 1-benzyl-5-oxoazepane-4-carboxylateHCID 17221604(3-Chlorophenyl)ethanimidamide

Product 1

HCID 136058092HCID 136058092, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethanol (30 ml) was cooled in an ice bath then sodium (160 mg, 6.70 mmol) was added, with vigorous stirring. Once the sodium was dissolved, 2-(3-chlorophenyl)ethanimidamide (474 mg, 2.81 mmol) and ethyl 1-benzyl-5-oxoazepane-4-carboxylate (876 mg, 2.81 mmol) was added. The reaction mixture was refluxed, under nitrogen, for 17 h. Water (2 ml) was added to quench the reaction then the reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate (20 ml) and water (20 ml). The organic phase was dried over magnesium sulphate and concentrated in vacuo. Trituration of the residue with diethyl ether afforded the title compound as a solid in 33% yield, 361 mg.

Workup

  1. temperatureThe reaction mixture was refluxed, under nitrogen, for 17 h
  2. customto quench
  3. customthe reaction
  4. concentrationthe reaction mixture was concentrated in vacuo
  5. customThe residue was partitioned between ethyl acetate (20 ml) and water (20 ml)
  6. dry with materialThe organic phase was dried over magnesium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d6030263b57c40c7aa24a41eaf67fb2c
Source dataset
uspto-grants-2011_04
Patent number
US07928099B2

Reaction notes

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