9-(4-Chloro-2-fluoro-5-nitrophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thione → 9-(5-Amino-4-chloro-2-fluorophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thione
Reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N:11]=[C:12]2[N:20]3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19]3)[C:14](=[S:21])[S:13]2)=[C:4]([F:22])[CH:3]=1>C(O)(=O)C.[Fe]>[NH2:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([F:22])=[C:5]([N:11]=[C:12]2[N:20]3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19]3)[C:14](=[S:21])[S:13]2)[CH:6]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 75 °C
Procedure
To a stirred, hot (75° C.) mixture of 1.4 g (0.025 mole) of iron powder in 200 mL of acetic acid was added 1.5 g (0.0042 mole) of 9-(4-chloro-2-fluoro-5-nitrophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thione. The mixture was stirred at 75° C. for one hour, then filtered and the filtrate evaporated under reduced pressure leaving a residue. The residue was partitioned between ethyl acetate and an aqueous, saturated sodium bicarbonate solution. The organic phase was separated, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated under reduced pressure to yield 1.1 g of 9-(5-amino-4-chloro-2-fluorophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thione as a solid, mp 59°-61° C.
Workup
- filtrationfiltered
- customthe filtrate evaporated under reduced pressure
- customleaving a residue
- customThe residue was partitioned between ethyl acetate
- customThe organic phase was separated
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customThe filtrate was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-83248548c50c4a038d5df084548c42cd
- Source dataset
- uspto-grants-1990_03
- Patent number
- US04906281
Reaction notes
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