Sodium Glycinate → HCID 21189951, compound

HRID 1068603Notes

Reaction equation

HRID 1068603 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. additionat 70° C., was added dropwise
  2. temperatureThe suspension was cooled to room temperature
  3. filtrationthe resulting red solid was filtered
  4. washwashed with chloroform (10 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-4f6bb1d1a4684a02bce3a663aa0fbcc6
Source dataset
uspto-grants-2001_06
Patent number
US06251903B1

Reaction notes

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