Sodium Hydroxide → 2-(benzo[d][1,3]dioxol-5-yl)-N-methoxy-N-methylacetamide

HRID 2244112Notes

Reaction equation

HRID 2244112 reaction equation
S(Cl)(Cl)=O.[O:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH2:14][C:15]([OH:17])=O)=[CH:13][C:8]=2[O:7][CH2:6]1.[OH-].[Na+].Cl.[CH3:21][NH:22][O:23][CH3:24].O1C2C=CC(CC(Cl)=O)=CC=2OC1>C1(C)C=CC=CC=1.O.CN(C)C=O>[O:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH2:14][C:15]([N:22]([O:23][CH3:24])[CH3:21])=[O:17])=[CH:13][C:8]=2[O:7][CH2:6]1

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 76115Benzo-1,3-dioxole-5-acetic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2756584Benzo(1,3)dioxol-5-yl-acetyl chloride

Product 1

HCID 149181612-(benzo[d][1,3]dioxol-5-yl)-N-methoxy-N-methylacetamideYield 95.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Thionyl chloride (39.6 g) and a drop of dimethylformamide were added to a solution of benzo(1,3)dioxol-5-yl-acetic acid (30.0 g) in toluene (200 ml) and then the mixture was stirred for 2.5 hours at 60° C., after distilling out the solvent, to yield unpurified benzo(1,3)dioxol-5-yl-acetyl chloride. A solution of sodium hydroxide (20.0 g) in water (150 ml) was added to a solution of N,O-dimethylhydroxylamine hydrochloride (19.5 g) in toluene (200 ml) at 0° C., and further the unpurified benzo(1,3)dioxol-5-yl-acetyl chloride was added thereto, and then the mixture was stirred for 3 hours. The reaction mixture was extracted with toluene and dried over anhydrous magnesium sulfate, and from which the solvent was evaporated to yield unpurified 2-benzo(1,3)dioxol-5-yl-N-methoxy-N-methylacetoamide (35.4 g).

Workup

  1. distillationafter distilling out the solvent
  2. customto yield unpurified benzo(1,3)dioxol-5-yl-acetyl chloride
  3. stirringthe mixture was stirred for 3 hours
  4. extractionThe reaction mixture was extracted with toluene
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customfrom which the solvent was evaporated

Sources & evidence

ORD record
ord-7c2591c86c8e4bcf9c12c9c670fca1e6
Source dataset
uspto-grants-2010_03
Patent number
US07678810B2

Reaction notes

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