Glycine → HCID 21189956, compound

HRID 1781010Notes

Reaction equation

HRID 1781010 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5](Cl)=[CH:4][C:3]=1[Br:12].C([O-])(O)=O.[Na+:17].[NH2:18][CH2:19][C:20]([OH:22])=[O:21]>CN(C=O)C.O>[Na+:17].[Br:12][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[C:5]([NH:18][CH2:19][C:20]([O-:22])=[O:21])[CH:4]=1

Participants

6

Reactant 3

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

Product 1

HCID 21189956HCID 21189956, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of 2,5-dichloro-4-nitrobromobenzene (1.000 g, 3.691 mmol, as prepared above) 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 room temperature, filtered, washed with water (1.0 mL), and dried under vacuum to afford 0.284 g (98%, based on recovered starting material) of the pure (1H NMR) title compound as an orange powder; m.p. 264°-265° C. (decomposed); 1H NMR (DMSO-d6): δ3.451 (d, 2H, J=3.9 Hz), 7.199 (s, 1H), 8.130 (s, 1H), 8.793 (t, 1H, J=3.6 Hz). It was used as such for the next reaction.

Workup

  1. temperatureThe bright orange suspension was then cooled to room temperature
  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 the pure (1H NMR) title compound as an orange powder
  7. customsuch for the next reaction

Sources & evidence

ORD record
ord-0b069435ba774dba9ff2497ddd53fbd5
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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