Ammonia → N'-(3-chlorophenyl)-2-ethoxyacetohydrazonamide

HRID 334027Notes

Reaction equation

HRID 334027 reaction equation
[NH3:1].Cl[C:3](=[N:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[C:4]([O:6][CH2:7][CH3:8])=O>C1COCC1>[Cl:17][C:13]1[CH:12]=[C:11]([NH:10][N:9]=[C:3]([NH2:1])[CH2:4][O:6][CH2:7][CH3:8])[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 580329Acetic acid, chloro[(3-chlorophenyl)hydrazono]-, ethyl ester

Product 1

HCID 86688257N'-(3-chlorophenyl)-2-ethoxyacetohydrazonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

45.0 mL (60.2 mmol) aqueous ammonia solution (25%) was added over 20 minutes to a solution of 15.0 g (57.4 mmol) ethyl 2-chloro-2-(2-(3-chlorophenyl)hydrazono)acetate in 75 mL THF and stirred for 1 h. The resulting mixture was diluted and extracted with hexane and EtOAc (1:1 mixture). The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated and used without further purification for the next synthesis step (yield: 12.0 g (92%)).

Workup

  1. additionThe resulting mixture was diluted
  2. extractionextracted with hexane and EtOAc (1:1 mixture)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customused without further purification for the next synthesis step (yield: 12.0 g (92%))

Sources & evidence

ORD record
ord-6e534e6c8aaf47f7a87be68906165cf7
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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