Sodium Glycinate → HCID 21190019, compound

HRID 1857441Notes

Reaction equation

HRID 1857441 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[F:12].[NH2:13][CH2:14][C:15]([O-:17])=[O:16].[Na+:18]>C(O)C.O>[Na+:18].[Cl:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:13][CH2:14][C:15]([O-:17])=[O:16])[CH:7]=1

Participants

5

Reactant 2

HCID 4684308Sodium GlycinateHCID 157514831-Chloro-2,5-difluoro-4-nitrobenzene

Product 1

HCID 21190019HCID 21190019, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 1-chloro-2,5-difluoro-4-nitrobenzene (0.825 g, 4.26 mmol) in ethanol (8.0 mL), was added a solution of sodium glycinate (0.415 g, 4.27 mmol) in water (1.5 mL). The resulting suspension was refluxed for 60 h. The solution was cooled to room temperature and the precipitated bright orange solid was filtered, washed with cold ethanol (5 mL), and dried under vacuum to give 0.673 g (64%) title compound as a bright orange powder; 1H NMR (DMSO-d6) δ 3.50 (d, 2H, J=3.6 Hz), 7.04 (d, 1H, J=6.6 Hz), 8.01 (d, 1H J=9.9 Hz), 8.74 (s, 1H). The unreacted 1-chloro-2,5-difluoro-4-nitrobenzene was recovered almost quantitatively from the filtrate.

Workup

  1. temperatureThe resulting suspension was refluxed for 60 h
  2. filtrationthe precipitated bright orange solid was filtered
  3. washwashed with cold ethanol (5 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-29992e6e48424e15907640a93fba2eb8
Source dataset
uspto-grants-2000_11
Patent number
US06147075

Reaction notes

Loading…