Ethanol → HCID 57908202, compound

HRID 1668849Notes

Reaction equation

HRID 1668849 reaction equation
[Cl:1][C:2]1[C:3]([N:10]([C:19](OC(C)(C)C)=O)[NH:11][C:12](OC(C)(C)C)=O)=[C:4]([F:9])[C:5]([F:8])=[N:6][CH:7]=1.[CH3:26]OC(OC)CC(OC)OC.CCO.OS(O)(=O)=O>CCOC(C)=O>[Cl:1][C:2]1[C:3]([N:10]2[CH:19]=[CH:26][CH:12]=[N:11]2)=[C:4]([F:9])[C:5]([F:8])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 66019TetramethoxypropaneHCID 57908198HCID 57908198, compound

Product 1

HCID 57908202HCID 57908202, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To a stirred mixture of di-tert-butyl 1-(5-chloro-2,3-difluoropyridin-4-yl)hydrazine-1,2-dicarboxylate (4.0 g, 0.010 mol, 1.0 equiv) and 1,1,3,3-tetramethoxypropane (17 mL, 0.10 mol, 10 equiv) was added a mixture of EtOH (100 mL) and concentrated H2SO4 (28 mL). The vessel was then sealed and heated to 45° C. After stirring for 45 minutes, the mixture was diluted with EtOAc (300 mL) and washed with water (300 mL), dried over Na2SO4 and concentrated under vacuum. The residue was purified over silica gel using 100% dichloromethane as eluent to give the desired product (1.6 g, 70%).

Workup

  1. additionwas added
  2. customThe vessel was then sealed
  3. washwashed with water (300 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified over silica gel using 100% dichloromethane as eluent

Sources & evidence

ORD record
ord-c5e3246d92644f25a650a687b94cd4d5
Source dataset
uspto-grants-2011_08
Patent number
US07989469B2

Reaction notes

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