2,6-Dimethylaniline → Glycine, N-(2,6-dimethylphenyl)-

HRID 1067737Notes

Reaction equation

HRID 1067737 reaction equation
CC1C=CC=C(C)C=1N.BrCC(OCC)=O.Br.[CH3:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=1[NH:26][CH2:27][C:28]([OH:30])=[O:29]>ClCCl>[CH3:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([CH3:18])[C:20]=1[NH:26][CH2:27][C:28]([OH:30])=[O:29]

Participants

5

Reactant 3

HCID 68962,6-DimethylanilineHCID 7748Ethyl bromoacetateHCID 21879725HCID 21879725, compound

Product 1

HCID 826274Glycine, N-(2,6-dimethylphenyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,6-Dimethylaniline (6.1 g, 50.4 mmol), and ethyl bromoacetate (8.4 g, 50.4 mmol) were refluxed neat for 10 min. The reaction mixture was cooled to room temperature and poured into dichloromethane (75 mL). A precipitated formed which was collected and triturated with dichloromethane (25 mL). N-(2,6-Dimethylphenyl)glycine hydrobromide salt (1.21 g, 4.6 mmol, 9.0%) was collected as a white crystalline solid. 1H NMR (CD3OD) d 2.48 (s, 6H), 4.29 (s, 2H), 7.00-7.10 (m, 3H).

Workup

  1. customA precipitated
  2. customformed which
  3. customwas collected
  4. customtriturated with dichloromethane (25 mL)

Sources & evidence

ORD record
ord-c3ace5e0af63405e81a972dd7da42145
Source dataset
uspto-grants-2001_06
Patent number
US06248775B1

Reaction notes

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