Sodium Glycinate → HCID 21190019, compound

HRID 1781061Notes

Reaction equation

HRID 1781061 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) δ3.50 (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-6af7050892d54175aa064b56c9f69106
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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