Water → HCID 18929940, compound

HRID 3126Notes

Reaction equation

HRID 3126 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-96c9427d56a846deb08ae5a7e598c8e7
Source dataset
uspto-grants-1998_03
Patent number
US05733910

Reaction notes

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