Hydrazine hydrate (1:1) → HCID 178502067, compound

HRID 1408429Notes

Reaction equation

HRID 1408429 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]=[CH:10][N:11](C)C)=[CH:4][C:3]=1[CH2:15][NH:16][C:17](=[O:20])[O:18][CH3:19].O.[NH2:22]N.CO.C(Cl)(Cl)Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][NH:11][N:22]=2)=[CH:4][C:3]=1[CH2:15][NH:16][C:17](=[O:20])[O:18][CH3:19]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 21584188Chloroform methanolHCID 66789975methyl N-[[2-chloro-5-[3-(dimethylamino)-1-oxo-2-propen-1-yl]phenyl]methyl]carbamate2×

Product 1

HCID 178502067HCID 178502067, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl N-[[2-chloro-5-[3-(dimethylamino)-1-oxo-2-propen-1-yl]phenyl]methyl]carbamate (i.e. the product of Step A) (10 g, 33.78 mmol) in methanol (100 mL) was added hydrazine hydrate (1.08 mL, 33.78 mmol) and the reaction mixture was stirred at ambient temperature for 2 days. After TLC analysis (10% MeOH/CHCl3) showed completion of the reaction, the reaction mixture was filtered was filtered. The resultant solid residue was washed with methanol and dried under vacuum to give the title compound (4 g, 48% yield) as solid.

Workup

  1. customcompletion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. filtrationwas filtered
  4. washThe resultant solid residue was washed with methanol
  5. customdried under vacuum

Sources & evidence

ORD record
ord-254496ca6b314b20827e854f5548e06a
Source dataset
uspto-grants-2014_12
Patent number
US08921360B2

Reaction notes

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