Water → Ethyl 7-oxoazepane-4-carboxylate

HRID 1620559Notes

Reaction equation

HRID 1620559 reaction equation
ClC1N=C(Cl)N=C(Cl)N=1.O[N:11]=[C:12]1[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1.[OH2:23]>CN(C=O)C>[O:23]=[C:12]1[NH:11][CH2:17][CH2:16][CH:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 7954Cyanuric chlorideHCID 11593553Cyclohexanecarboxylic acid, 4-(hydroxyimino)-, ethyl ester

Product 1

HCID 23093698Ethyl 7-oxoazepane-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2,4,6-trichloro-1,3,5-triazine (21.7 g) in DMF (25 mL) was added dropwise ethyl 4-(hydroxyimino)cyclohexanecarboxylate (27.2 g) in DMF (220 mL) over 30 min. The mixture was stirred at room temperature overnight, poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give ethyl 7-oxoazepane-4-carboxylate (2.40 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a6a4d4f17f4649ec96abe580df828ef6
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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