Aniline → HCID 21693963, compound

HRID 482929Notes

Reaction equation

HRID 482929 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])(=O)C.[Na+]>CN(C)C=O>[C:14]1([NH:13][CH2:2][C:3]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 62576Benzyl bromoacetateHCID 517045Sodium Acetate

Product 1

HCID 21693963HCID 21693963, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzyl bromoacetate (4.0 ml) and aniline (2.28 ml) in 25 ml of dry dimethylformamide was added sodium acetate (2.05 g). The reaction was stirred at room temperature overnight and extracted from water with three portions of ethyl acetate. The combined organic layers were washed with water and dried over sodium sulfate. The volatiles were removed, and the residue was purified by flash column chromatography on silica gel (eluting with 10% ethyl acetate/hexane) to yield 4.54 g of benzyl N-phenylglycinate.

Workup

  1. extractionextracted from water with three portions of ethyl acetate
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over sodium sulfate
  4. customThe volatiles were removed
  5. customthe residue was purified by flash column chromatography on silica gel (eluting with 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-300e4601a02a4e33b59ba337c0626923
Source dataset
uspto-grants-1986_03
Patent number
US04576749

Reaction notes

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