Chlorosuccinimide → ethyl (2Z)-2-chloro-2-[(2-fluorophenyl)methylhydrazinylidene]acetate

HRID 1640336Notes

Reaction equation

HRID 1640336 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][NH:5]/[N:6]=[CH:7]/[C:8]([O:10][CH2:11][CH3:12])=[O:9].[Cl:17]N1C(=O)CCC1=O>C(OCC)(=O)C>[Cl:17]/[C:7](=[N:6]\[NH:5][CH2:4][C:3]1[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=1[F:1])/[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 58142729HCID 58142729, compound

Product 1

HCID 58142732ethyl (2Z)-2-chloro-2-[(2-fluorophenyl)methylhydrazinylidene]acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl (2E)-[(2-fluorobenzyl)hydrazono]acetate (300 mg, 1.14 mmol) from example 1A are dissolved in ethyl acetate (2.0 ml). N-Chlorosuccinimide (143 mg, 1.07 mmol) is added, and the mixture is stirred at 60° C. for 1 h. It is then concentrated in vacuo, and the residue is stirred with carbon tetrachloride. The filtrate after filtration is concentrated. 292 mg (82% of theory) of the desired compound are obtained.

Workup

  1. concentrationIt is then concentrated in vacuo
  2. stirringthe residue is stirred with carbon tetrachloride
  3. filtrationThe filtrate after filtration
  4. concentrationis concentrated

Sources & evidence

ORD record
ord-eb07e1143933489ab3f13ef26e9f9baa
Source dataset
uspto-grants-2012_02
Patent number
US08114400B2

Reaction notes

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