Hydrazine hydrate (1:1) → (3-Bromothien-2-yl) (3-methoxyphenyl)methanone hydrazone
Reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)=O.O.[NH2:18][NH2:19]>C(O)CO>[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)=[N:18][NH2:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
A mixture of (3-bromothien-2-yl) (3-methoxyphenyl)methanone (10.0 g), hydrazine hydrate (10 ml, above 99% purity), and 75 ml of ethylene glycol was heated at 130° C. for three hours. The reaction mixture was then quenched with water and extracted with ether. The ether solution was washed three times with water and dried over anhydrous magnesium sulfate. The ether was then evaporated to give 5.5 g of an oil. This was then column chromatographed on a silica gel column packed in hexane using 15% ether/hexane as an eluent. The solid from the column was then recrystallized from ether/hexane.
Workup
- customThe reaction mixture was then quenched with water
- extractionextracted with ether
- washThe ether solution was washed three times with water
- dry with materialdried over anhydrous magnesium sulfate
- customThe ether was then evaporated
Sources & evidence
- ORD record
- ord-5a3cc12a0ba4437fbb450989dc1c7986
- Source dataset
- uspto-grants-1988_09
- Patent number
- US04769472
Reaction notes
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