Dichloromethane → HCID 53669213, compound

HRID 1505485Notes

Reaction equation

HRID 1505485 reaction equation
[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([F:14])[C:3]=1C(O)=O.ClCCl.[C:18](Cl)(=[O:22])C(Cl)=O.[N-:24]=[N+]=[N-].[Na+].[C:28]([OH:32])([CH3:31])([CH3:30])[CH3:29]>CN(C)C=O>[C:28]([O:32][C:18](=[O:22])[NH:24][C:3]1[C:7]([F:14])=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]=1[F:1])([CH3:31])([CH3:30])[CH3:29]

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 6386tert-ButanolHCID 33557Sodium AzideHCID 65578Oxalyl chlorideHCID 3026292,6-Difluoro-3-nitrobenzoic acid

Product 1

HCID 53669213HCID 53669213, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 2,6-difluoro-3-nitro benzoic acid (16 g, 79 mmol) prepared at Step 1 was added into a mixed solvent of dichloromethane and N,N-dimethylformamide and oxalyl chloride (14 mL, 158 mmol) was applied slowly. After stirring the reactant at room temperature for 18 hours and concentrating the solvent, the residuals were diluted with dichloromethane and N,N-dimethylformamide and the temperature was lowered to 0° C. Sodium azide (5.6 g, 87 mmol) was added gradually and slowly. After stirring at room temperature for 30 minutes, tert-butanol (40 mL) was applied. The reactant was refluxed and stirred for 3 hours. After the reaction, the solvent was vacuum concentrated. After the concentration, the residuals were washed with an aqueous solution of sodium hydrogen carbonate and salt water and extracted with ethylacetate, and the organic matter was concentrated and dried with sulfuric anhydride magnesium, and then refined by means of column chromatography, so that 20 g of the target compound, tert-butyl-2,6-difluoro-3-nitrophenylcarbamate (percentage yield: 93%), was obtained

Workup

  1. concentrationconcentrating the solvent
  2. additionthe residuals were diluted with dichloromethane and N,N-dimethylformamide
  3. customwas lowered to 0° C
  4. stirringAfter stirring at room temperature for 30 minutes
  5. temperatureThe reactant was refluxed
  6. stirringstirred for 3 hours
  7. customAfter the reaction
  8. concentrationconcentrated
  9. concentrationAfter the concentration
  10. washthe residuals were washed with an aqueous solution of sodium hydrogen carbonate and salt water
  11. extractionextracted with ethylacetate
  12. concentrationthe organic matter was concentrated
  13. dry with materialdried with sulfuric anhydride magnesium

Sources & evidence

ORD record
ord-48c0f0ed596948c6b8249b2b6fdd9f61
Source dataset
uspto-grants-2015_12
Patent number
US09216981B2

Reaction notes

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