Sodium Thiosulfate → Ethyl 3-[1-(2-amino-4-fluorophenyl)-1H-imidazol-2-yl]-propanoate

HRID 576857Notes

Reaction equation

HRID 576857 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:4]([N+:20]([O-])=O)[CH:3]=1.[O-]S([O-])(=S)=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C.O>[NH2:20][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 59198877Ethyl 3-[1-(4-fluoro-2-nitrophenyl)-1H-imidazol-2-yl]-propanoate

Product 1

HCID 59198670Ethyl 3-[1-(2-amino-4-fluorophenyl)-1H-imidazol-2-yl]-propanoate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Ethyl 3-[1-(4-fluoro-2-nitrophenyl)-1H-imidazol-2-yl]-propanoate as synthesized in above Production Example 91, 210 mg was dissolved in 1 mL of acetic acid and 1 mL of water, to which 533 mg of 85% sodium hyposulfite was added, followed by 2.5 hours' heating under reflux. The reaction liquid was allowed to cool off and rendered weakly alkaline with saturated aqueous sodium hydrogencarbonate solution, which was extracted with ethyl acetate. The extract was washed with saturated brine and dried over sodium sulfate. Distilling the solvent off under reduced pressure, 100 mg of the title compound was obtained.

Workup

  1. temperature' heating
  2. temperatureunder reflux
  3. customThe reaction liquid
  4. temperatureto cool off
  5. extractionwas extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-0431cbefd74047c6be32c64dd8ae87ee
Source dataset
uspto-grants-2015_05
Patent number
US09040536B2

Reaction notes

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