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

HRID 72770Notes

Reaction equation

HRID 72770 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-b2425c5fb69e4662b0101c5da5e11ed3
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Reaction notes

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