Ethyl bromoacetate → HCID 68143097, compound

HRID 1579728Notes

Reaction equation

HRID 1579728 reaction equation
Cl.[CH3:2][NH:3][CH2:4][C:5]([NH:7][C:8]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11])=[O:6].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[ClH:22].[C:25]([CH2:24][N:3]([CH3:2])[CH2:4][C:5]([NH:7][C:8]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11])=[O:6])([O:27][CH2:28][CH3:29])=[O:26]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 68141832HCID 68141832, compound

Product 1

HCID 68143097HCID 68143097, compoundYield 122%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.7 g of 2-(methylamino-acetamido)-5-chlorobenzophenone hydrochloride, 0.85 g of ethyl bromacetate and 0.7 g of anhydrous potassium carbonate were heated for 20 hours under a reflux in 100 mls. of anhydrous acetone whilst stirring. After cooling, the inorganic salt was filtered off under suction concentrated in vacuo, and the oily residue was dried in vacuo. The yield of oily crude base was 1.4 g. It was dissolved in 30 mls. of absolute dioxane, the solution was filtered and diluted with 30 mls. absolute ether, 1.3 g of 2-(4-carbethoxy-3-methyl-3-aza-butyramido)-5-chlorobenzophenone hydrochloride with a melting point of 178°-180° being obtained by passing in dry hydrogen chloride. The product was identical with that obtained in Example 5.

Workup

  1. temperaturea reflux in 100 mls
  2. temperatureAfter cooling
  3. filtrationthe inorganic salt was filtered off under suction
  4. concentrationconcentrated in vacuo
  5. customthe oily residue was dried in vacuo
  6. dissolutionIt was dissolved in 30 mls
  7. filtrationof absolute dioxane, the solution was filtered
  8. additiondiluted with 30 mls

Sources & evidence

ORD record
ord-5f0ec6214ab7442f8d7193d1402ec7d8
Source dataset
uspto-grants-1976_01
Patent number
US03931301

Reaction notes

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