Oxalic Acid → HCID 12812488, compound

HRID 2164523Notes

Reaction equation

HRID 2164523 reaction equation
C(O)(=O)/C=C\C(O)=O.[CH3:9][CH:10]([N:17]1[CH2:20][CH:19]([OH:21])[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[H-].[Na+].[Cl:24][C:25]1[CH:26]=[C:27](F)[CH:28]=[CH:29][CH:30]=1.[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34]>[K].CN(C)C=O>[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34].[Cl:24][C:25]1[CH:30]=[C:29]([CH:28]=[CH:27][CH:26]=1)[O:21][CH:19]1[CH2:20][N:17]([CH:10]([CH3:9])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:18]1

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 24758Sodium hydrideHCID 2230871-Chloro-3-fluorobenzeneHCID 12812484HCID 12812484, compound

Product 1

HCID 12812488HCID 12812488, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 5462222PotassiumSolvent

Conditions

Temperature
90 °C

Procedure

1-(α-Methylbenzyl)-3-hydroxyazetidine maleate (393 g., 1.3 moles) was partitioned in dilute potassium hydroxidebenzene. The separated dried benzene solution was concentrated, the residual oil dissolved in 250 ml. of dimethylformamide and added dropwise to a stirred suspension of 53 g. (1.1 moles) of 50% sodium hydride in 750 ml. of dimethylformamide at 90° C. The mixture was heated at 90° C. for 1 hr. and 130.5 g. (1 mole) of 3-chlorofluorobenzene added dropwise at 90° C. The mixture was refluxed for 3 hrs., cooled and partitioned between isopropyl ether and dilute sodium hydroxide. The isopropyl ether solution was dried, concentrated, and the residue added to 1200 ml. of isopropyl alcohol containing 90 g. (1 mole) of oxalic acid. The oxalate salt was recrystallized from ethanol. Yield 263 g. (69%); m.p. 141°-144° C.

Workup

  1. concentrationThe separated dried benzene solution was concentrated
  2. dissolutionthe residual oil dissolved in 250 ml
  3. additionof dimethylformamide and added dropwise to a stirred suspension of 53 g
  4. customat 90° C
  5. temperatureThe mixture was refluxed for 3 hrs
  6. temperature, cooled
  7. custompartitioned between isopropyl ether and dilute sodium hydroxide
  8. dry with materialThe isopropyl ether solution was dried
  9. concentrationconcentrated
  10. additionthe residue added to 1200 ml
  11. customThe oxalate salt was recrystallized from ethanol

Sources & evidence

ORD record
ord-623e1629b9fa44639f6457787ff0bf4c
Source dataset
uspto-grants-1985_03
Patent number
US04505907

Reaction notes

Loading…