Water → HCID 86632897, compound

HRID 1398874Notes

Reaction equation

HRID 1398874 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[NH2:14][CH2:15][C:16]([F:21])([F:20])[C:17]([OH:19])=[O:18].C(=O)([O-])O.[Na+].O>CO>[N+:11]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH:14][CH2:15][C:16]([F:21])([F:20])[C:17]([OH:19])=[O:18])([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 118141-Chloro-2,6-dinitrobenzeneHCID 516892Sodium Bicarbonate2×HCID 27564053-Amino-2,2-difluoropropanoic acid

Product 1

HCID 86632897HCID 86632897, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-1,3-dinitrobenzene (2.94 g, 14.54 mmol) in methanol (30.0 mL) were added 3-amino-2,2-difluoropropanoic acid (2.0 g, 15.99 mmol), sodium hydrogen carbonate (2.69 g, 31.98 mmol) and water (15 mL). The reaction mixture was stirred at 80° C. for 1 day. The starting material wasn't consumed completely. To the mixture was added sodium hydrogen carbonate (5.88 g, 63.96 mmol) and the mixture was stirred at 80° C. for 0.5 day. After cooling, the solvent was removed. The residue was neutralized with 1N hydrochloric acid (100 mL) and extracted with ethyl acetate (×3). The combined organic layer was washed with brine (×1), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the title compound as a yellow solid (3.52 g, 12.09 mmol, 83%).

Workup

  1. customThe starting material wasn't consumed completely
  2. stirringthe mixture was stirred at 80° C. for 0.5 day
  3. temperatureAfter cooling
  4. customthe solvent was removed
  5. extractionextracted with ethyl acetate (×3)
  6. washThe combined organic layer was washed with brine (×1)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e4e65e3515d43d1bfa5c2a2a54791dd
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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