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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

HRID 1164711
Notes
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Reaction equation

HRID 1164711 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]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 146229569-(4-Chloro-2-fluoro-5-nitrophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thione

Product 1

HCID 146229579-(5-Amino-4-chloro-2-fluorophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thioneYield 79.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

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

  1. filtrationfiltered
  2. customthe filtrate evaporated under reduced pressure
  3. customleaving a residue
  4. customThe residue was partitioned between ethyl acetate
  5. customThe organic phase was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-83248548c50c4a038d5df084548c42cd
Source dataset
uspto-grants-1990_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04906281

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes