Hydrazine hydrate (1:1) → HCID 178509230, compound
Reaction equation
Cl[C:2]1[N:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[C:4]#[N:5].O.[NH2:12][NH2:13]>C(O)CCC>[F:10][C:7]1[CH:6]=[C:3]2[C:4]([NH2:5])=[N:13][NH:12][C:2]2=[N:9][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of compound 4 (50 g, 321.7 mmol) in 1-butanol (1 L) was added hydrazine monohydrate (150 mL, 3.2 mol), and the mixture was refluxed for 4 h. The mixture was cooled to room temperature and concentrated. The precipitate was successively washed on filter with water (2×) and Et2O (2×) and dried in vacuo overnight to give compound 5 (44 g, 88%) as a yellow solid. 1H NMR (DMSO-d6, 300 MHz): δ 5.53 (s, 2H); 7.94 (dd, 1H); 8.35 (dd, 1H); 12.02 (s, 1H).
Workup
- temperaturethe mixture was refluxed for 4 h
- concentrationconcentrated
- washThe precipitate was successively washed
- filtrationon filter with water (2×) and Et2O (2×)
- customdried in vacuo overnight
Sources & evidence
- ORD record
- ord-da548bb149134ec9bf32bdb5af85a23a
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08242272B2
Reaction notes
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