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

HRID 2228867Notes

Reaction equation

HRID 2228867 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-4597048a62164f5b9ef534ffe575fd73
Source dataset
uspto-grants-2002_07
Patent number
US06417387B1

Reaction notes

Loading…