Dichloromethane → HCID 68597366, compound

HRID 573376Notes

Reaction equation

HRID 573376 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([CH2:16]O)[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:18]CCl.S(Cl)(Cl)=O.C(=O)(O)[O-].[Na+]>O.N1C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([CH2:16][Cl:18])[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 68598233HCID 68598233, compound

Product 1

HCID 68597366HCID 68597366, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a mixture of 0.74 g (2.9 mmol) of 2-(t-butoxycarbonyl)amino-4-chloro-6-hydroxymethylpyridine and 20 mL of dichloromethane 20 mL, 0.29 g (3.7 mmol) of pyridine was added, and 0.41 g (3.5 mmol) of thionyl chloride was further added, followed by stirring at room temperature for 3.5 hours. The reaction solution was added to water and saturated sodium bicarbonate aqueous solution was added thereby adjusting the pH to 6, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The resultant residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1 (v/v)) to obtain 0.56 g (2.0 mmol, yield of 71%) of 2-(t-butoxycarbonyl)amino-4-chloro-6-chloromethylpyridine.

Workup

  1. additionwas added
  2. additionwas added
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1 (v/v))

Sources & evidence

ORD record
ord-bdaefc637dbb4108ba4faf5765fd2f10
Source dataset
uspto-grants-2015_05
Patent number
US09029552B2

Reaction notes

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