HCID 67148759, compound → HCID 86632363, compound

HRID 2428140Notes

Reaction equation

HRID 2428140 reaction equation
[CH3:1][O:2][C:3](=[O:15])[NH:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([CH2:13][OH:14])[CH:7]=1>CC#N.O=[Mn]=O>[CH3:1][O:2][C:3](=[O:15])[NH:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([CH:13]=[O:14])[CH:7]=1

Participants

4

Reactant 1

HCID 67148759HCID 67148759, compound

Product 1

HCID 86632363HCID 86632363, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst3×HCID 6342AcetonitrileSolvent

Procedure

MnO2 (6.68 g, 76.9 mmol) was added to a sol. of (4-chloro-3-hydroxymethyl-benzyl)-carbamic acid methyl ester (3.53 g, 15.4 mmol) in CH3CN (300 mL). The mixture was stirred at rt for 3 h, and MnO2 (2.67 g, 30.7 mmol) was added again. The mixture was stirred for 1 h, and MnO2 (1.34 g, 15.4 mmol) was added again. The mixture was stirred for 2 h, and was filtered through celite. The precipitate was washed with CH2Cl2, and the filtrate was evaporated under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (3.22 g, 92%) that was used further without purification.

Workup

  1. stirringThe mixture was stirred for 1 h
  2. stirringThe mixture was stirred for 2 h
  3. filtrationwas filtered through celite
  4. washThe precipitate was washed with CH2Cl2
  5. customthe filtrate was evaporated under reduced pressure
  6. customDrying the residue under high vacuum

Sources & evidence

ORD record
ord-15939496b77c40dda8604bb577d8d85f
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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