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

HRID 479731Notes

Reaction equation

HRID 479731 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-0211fa802adf43b4afe9c8b228f8484d
Source dataset
uspto-grants-2003_11
Patent number
US06646010B2

Reaction notes

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