Sodium Glycinate → HCID 21189951, compound

HRID 1600715Notes

Reaction equation

HRID 1600715 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5](F)=[CH:4][C:3]=1[CH3:12].[NH2:13][CH2:14][C:15]([O-:17])=[O:16].[Na+:18]>CN(C=O)C.O>[Na+:18].[Cl:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([NH:13][CH2:14][C:15]([O-:17])=[O:16])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 2

HCID 4684308Sodium GlycinateHCID 103524921-Chloro-4-fluoro-2-methyl-5-nitrobenzene

Product 1

HCID 21189951HCID 21189951, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 2-chloro-5-fluoro-4-nitrotoluene (0.605 g, 3.19 mmol, as prepared above) in DMF (3.0 mL) at 70° C., was added dropwise, a solution of sodium glycinate (0.310 g, 3.19 mmol, Aldrich, used as received) in water (3.0 mL). The resulting suspension was stirred overnight at 70° C. The suspension was cooled to room temperature and the resulting red solid was filtered, washed with chloroform (10 mL) and dried under vacuum to give 0.360 g (46%) pure (1H NMR) title compound as a red powder; 1H NMR (DMSO-d6): δ 2.276 (s, 3H), 3.431 (d, 2H, J=4.2 Hz), 6.848 (s, 1H), 7.963 (s, 1H), 8.773 (s, 1H).

Workup

  1. temperatureThe suspension was cooled to room temperature
  2. filtrationthe resulting red solid was filtered
  3. washwashed with chloroform (10 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-c6ffc241448b4bb290ef3350fd092107
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

Loading…