Water → HCID 18929940, compound

HRID 1449574Notes

Reaction equation

HRID 1449574 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[C:16]([Cl:18])[C:15]([O:19][CH3:20])=[C:14]([Cl:21])[C:10]=1[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:25].O>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[C:16]([Cl:18])[C:15]([O:19][CH3:20])=[C:14]([Cl:21])[C:10]=1[C:11]([O:13][CH3:25])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18929872HCID 18929872, compound

Product 1

HCID 18929940HCID 18929940, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cold (ice bath) stirred solution of 2-(tert-butoxycarbonylamino)-4,6-dichloro-5-methoxybenzoic acid (2.0 g, 5.9 mM) in 20 mL of dry dimethylformamide under a nitrogen atmosphere was added sodium hydride (0.24 g, 5.9 mM); a precipitate formed which slowly redissolved on stirring. To the resulting stirred solution was added iodomethane (8.4 g, 59 mM). After stirring at room temperature for 1.5 hr, the reaction mixture was poured into water and the resulting mixture extracted with ether. The combined ether extracts were washed with brine, dried (MgSO4), filtered and concentrated to leave the title compound as a yellow oil (2.0 g, 96%); MS(CI): 350 (M+H).

Workup

  1. customa precipitate formed which
  2. dissolutionslowly redissolved
  3. stirringTo the resulting stirred solution
  4. stirringAfter stirring at room temperature for 1.5 hr
  5. extractionthe resulting mixture extracted with ether
  6. washThe combined ether extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ac1d39e153dc4fa684786e7489a03ba1
Source dataset
uspto-grants-1997_02
Patent number
US05599814

Reaction notes

Loading…