Phenylacetyl chloride → N-(2,2-dimethoxyethyl)-N-methyl-2-phenylacetamide

HRID 2376617Notes

Reaction equation

HRID 2376617 reaction equation
[CH3:1][O:2][CH:3]([O:7][CH3:8])[CH2:4][NH:5][CH3:6].C(=O)(O)[O-].[Na+].[C:14]1([CH2:20][C:21](Cl)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC(OC)(C)C.O>[CH3:6][N:5]([CH2:4][CH:3]([O:7][CH3:8])[O:2][CH3:1])[C:21](=[O:22])[CH2:20][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 85032,2-DimethoxyethylmethylamineHCID 516892Sodium Bicarbonate2×

Product 1

HCID 3423225N-(2,2-dimethoxyethyl)-N-methyl-2-phenylacetamideYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent2×

Procedure

To a 20 L Morton flask was added MTBE (5.52 L, 7 volumes) and (N-methyl-amino)-acetaldehyde dimethyl acetal (614 g, 5 mol) to form a solution at room temperature. A solution of sodium bicarbonate prepared by the addition of sodium bicarbonate (546 g, 6.5 mol) and water (6.31 L, 8 volume) was added to the Morton reaction flask. The mixture was cooled to less than 10° C and a MTBE (789 mL) solution of phenylacetyl chloride (789 g, 5 mol) was added dropwise to the cooled reaction mixture over a 1 h period. After addition, the reaction mixture was stirred at room temperature for 1 h. At this stage an HPLC analysis indicated that the reaction was completed. Extractive workup with MTBE (4 volumes), anhydrous magnesium sulfate drying followed by concentration on the rotary evaporator provided 1.187 kg (98%) of N-methyl-N-(2,2-dimethoxyethyl)phenylacetamide as a liquid, (M+H)+=237.9.

Workup

  1. customto form a solution at room temperature
  2. additionwas added to the Morton reaction flask
  3. temperatureThe mixture was cooled to less than 10° C
  4. additionAfter addition
  5. concentrationExtractive workup with MTBE (4 volumes), anhydrous magnesium sulfate drying followed by concentration on the rotary evaporator

Sources & evidence

ORD record
ord-44aeae1355ed44c387c1e1fc326e1c97
Source dataset
uspto-grants-2008_12
Patent number
US07468365B2

Reaction notes

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