Dimethyl Sulfate → Methyl 4-acetamido-3-allyl-5-chloro-2-methoxybenzoate

HRID 2074000Notes

Reaction equation

HRID 2074000 reaction equation
[CH2:1]([C:4]1[C:5]([OH:19])=[C:6]([CH:11]=[C:12]([Cl:18])[C:13]=1[NH:14][C:15](=[O:17])[CH3:16])[C:7]([O:9][CH3:10])=[O:8])[CH:2]=[CH2:3].[H-].[Na+].S(OC)(O[CH3:26])(=O)=O>CN(C=O)C>[CH2:1]([C:4]1[C:5]([O:19][CH3:26])=[C:6]([CH:11]=[C:12]([Cl:18])[C:13]=1[NH:14][C:15](=[O:17])[CH3:16])[C:7]([O:9][CH3:10])=[O:8])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 14883225Methyl 4-acetamido-3-allyl-5-chloro-2-hydroxybenzoate

Product 1

HCID 10709158Methyl 4-acetamido-3-allyl-5-chloro-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the phenolic compound of step 6 above (4 g) and NaH (0.7 g) in DMF (50 ml) is stirred for 15 minutes. Dimethyl sulfate (2 g) is added and the mixture is stirred for 16 hours. The mixture is partitioned between CH2Cl2 and H2O, and the organic layer is separated and washed with H2O, dried (MgSO4) and evaporated. The solid residue is twice recrystallized from MeOH-H2O and chromatographed on silica gel affording the desired product which is used in the next step.

Workup

  1. stirringthe mixture is stirred for 16 hours
  2. customThe mixture is partitioned between CH2Cl2 and H2O
  3. customthe organic layer is separated
  4. washwashed with H2O
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe solid residue is twice recrystallized from MeOH-H2O
  8. customchromatographed on silica gel affording the desired product which

Sources & evidence

ORD record
ord-21d8aa6f872545a09adbca85d2bb5350
Source dataset
uspto-grants-1990_04
Patent number
US04920219

Reaction notes

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