Chlorosuccinimide → HCID 86607133, compound

HRID 729401Notes

Reaction equation

HRID 729401 reaction equation
[C:1]([O:5][C:6]([N:8]([C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH2:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:18]N1C(=O)CCC1=O>C(O)(=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:9][Cl:18])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 69074930HCID 69074930, compound

Product 1

HCID 86607133HCID 86607133, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of a benzoylhydrazinecarboxylic acid tert-butyl ester (Example 7) in acetic acid (5 mL) is added N-chlorosuccinimide (1.2 eq.). After 1 hour, the reaction mixture is diluted with ethyl acetate and washed with saturated NaHCO3, water, and brine. The organic layer is dried over MgSO4 and filtered. The filtrate is concentrated under vacuum and purified via flash column chromatography (ethyl acetate/hexanes) to afford the corresponding chloro-benzoylhydrazinecarboxylic acid tert-butyl ester.

Workup

  1. washwashed with saturated NaHCO3, water, and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated under vacuum
  5. custompurified via flash column chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-56f78cc5d64440709c1d7f874e16572d
Source dataset
uspto-grants-2009_09
Patent number
US07582627B2

Reaction notes

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