Glycine → N-(5-Bromo-4-chloro-2-nitrophenyl)glycine

HRID 54403Notes

Reaction equation

HRID 54403 reaction equation
[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[C:4](Cl)[CH:3]=1.C([O-])(O)=O.[Na+].[NH2:18][CH2:19][C:20]([OH:22])=[O:21]>CN(C=O)C.O>[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[C:4]([NH:18][CH2:19][C:20]([OH:22])=[O:21])[CH:3]=1

Participants

6

Reactant 3

HCID 750GlycineHCID 516892Sodium BicarbonateHCID 211900161-Bromo-2,5-dichloro-4-nitrobenzene

Product 1

HCID 10063959N-(5-Bromo-4-chloro-2-nitrophenyl)glycine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of 4-bromo-2,5-dichloronitrobenzene (1.000 g, 3.691 mmol) in DMF (10.0 mL) at 65° C. was added dropwise a solution of NaHCO3 (0.316 g, 3.76 mmol) and glycine (0.280 g, 3.73 mmol, Aldrich, used as received) in water (3.8 mL). The resulting suspension was stirred at 65° C. for 65 h. The bright orange suspension was then cooled to r.t., filtered, washed with water (1.0 mL) and dried under vacuum to afford 0.284 g (98%, based on recovered starting material) of pure title compound as an orange powder; m.p. 264°-265° C. (decomposed); 1H NMR (DMSO-d6): 3.451 (d, 2H, J=3.9 Hz), 7.199 (s, 1H), 8.130 (s, 1H), 8.793 (t, 1H, J=3.6 Hz).

Workup

  1. temperatureThe bright orange suspension was then cooled to r.t.
  2. filtrationfiltered
  3. washwashed with water (1.0 mL)
  4. customdried under vacuum
  5. customto afford
  6. custom0.284 g (98%, based on recovered starting material) of pure title compound as an orange powder

Sources & evidence

ORD record
ord-27f1bdcc20ce4cd283b9fc78b15439e5
Source dataset
uspto-grants-1997_04
Patent number
US05622952

Reaction notes

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