Chlorosuccinimide → HCID 19853900, compound

HRID 1650379Notes

Reaction equation

HRID 1650379 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-5b0dde3983e14bd88069ec982c413e00
Source dataset
uspto-grants-1990_05
Patent number
US04924010

Reaction notes

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