Chlorosuccinimide → HCID 19853900, compound

HRID 1723059Notes

Reaction equation

HRID 1723059 reaction equation
[C:1]([NH:4][C:5]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:9]=2[C:8]([C:16]([O:18][CH3:19])=[O:17])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Cl:20]N1C(=O)CCC1=O>CN(C=O)C.C(OCC)(=O)C>[C:1]([NH:4][C:5]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:9]=2[C:8]([C:16]([O:18][CH3:19])=[O:17])=[CH:7][C:6]=1[Cl:20])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 14502105HCID 14502105, compound

Product 1

HCID 19853900HCID 19853900, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5 g (19.0 mmol) of methyl 6-acetylamino-2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylate from Example 26 in 10 ml DMF is added 3.0 g (22.8 mmol) of N-chlorosuccinimide in a single portion at room temperature. The resulting solution is allowed to stir 24 hours at room temperature. The reaction mixture is diluted with ethyl acetate and washed with water. The organic layer is dried over MgSO4, filtered, concentrated and subjected to flash chromatography (20% EtOAc/hexanes) to yield methyl 6-acetylamino-7-chloro-2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylate. This is used in the next step.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ecda336a30e94d2b80bac76302b41e33
Source dataset
uspto-grants-1989_08
Patent number
US04859683

Reaction notes

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