Aminoacetaldehyde dimethyl acetal → N-(2,2-dimethoxyethyl)-3-fluoro-4-nitro-benzamide

HRID 880504Notes

Reaction equation

HRID 880504 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].C(=O)(O)[O-].[Na+].[F:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[N+:23]([O-:25])=[O:24])[C:17](Cl)=[O:18]>O1CCCC1>[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH:5][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:22]([N+:23]([O-:25])=[O:24])=[C:14]([F:13])[CH:15]=1

Participants

5

Reactant 3

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 516892Sodium BicarbonateHCID 27746563-Fluoro-4-nitrobenzoyl chloride

Product 1

HCID 55103942N-(2,2-dimethoxyethyl)-3-fluoro-4-nitro-benzamideYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled solution of amino acetaldehyde dimethyl acetal (0.91 mL, 8.30 mmol) in dry tetrahydrofuran (15 mL) was added sodium bicarbonate (769 mg, 9.16 mmol) and then a solution of 3-fluoro-4-nitro-benzoyl chloride (1.7 g, 8.30 mmol) in dry tetrahydrofuran (15 mL) was added dropwise at 0° C. over a period of 30 min. The reaction mixture was stirred overnight at ambient temperature, the solvent was removed in vacuo, and the residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate and concentrated to yield N-(2,2-dimethoxyethyl)-3-fluoro-4-nitro-benzamide (2.0 g, 90%) as a brown liquid.

Workup

  1. customthe solvent was removed in vacuo
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-04c7b18cf44d467fb5570f91c6069339
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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