Methanol → HCID 13505729, compound

HRID 1732033Notes

Reaction equation

HRID 1732033 reaction equation
C(O)(=O)CCC(O)=O.[NH2:9][C:10]1[C:27]([Cl:28])=[CH:26][C:13]([C:14]([NH:16][CH:17]2[CH2:21][N:20](CC)[N:19]([CH2:24][CH3:25])[CH2:18]2)=[O:15])=[C:12]([O:29][CH3:30])[CH:11]=1.CO.Cl[O-].[Na+]>C(Cl)(Cl)Cl>[NH2:9][C:10]1[C:27]([Cl:28])=[CH:26][C:13]([C:14]([NH:16][CH:17]2[CH2:18][N:19]([CH2:24][CH3:25])[N:20]=[CH:21]2)=[O:15])=[C:12]([O:29][CH3:30])[CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6917727106613-26-7HCID 23665760Sodium Hypochlorite

Product 1

HCID 13505729HCID 13505729, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 8.90 g (0.020 mole) of 4-amino-5-chloro-N-(1,2-diethyl-4-pyrazolidinyl)-2-methoxybenzamide succinate in 400 ml of reagent grade methanol, cooled to -20° C. and under nitrogen atmosphere was added dropwise 80 ml of 5% aqueous sodium hypochlorite over a 20 min period while maintaining the reaction mixture at -20° C. The reaction mixture was stirred for an additional one hour period at 0° C. then diluted with one liter of chloroform. The diluted mixture was washed with 500 ml of water. The aqueous layer was extracted with 200 ml of chloroform. The combined chloroform layers were dried over sodium sulfate and concentrated in vacuo. The crude product was partially purified by column chromatography on a silica column (eluted with ethyl acetate:hexane:methanol, 4.5:4.5:1). Further purification was effected by high pressure liquid chromatography, using the same solvent system as eluant. On evaporation, the residue was triturated with cold diethyl ether to give 1.90 g (32.0%) of title product, m.p. 132.5°-134.0° C.

Workup

  1. washThe diluted mixture was washed with 500 ml of water
  2. extractionThe aqueous layer was extracted with 200 ml of chloroform
  3. dry with materialThe combined chloroform layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was partially purified by column chromatography on a silica column (eluted with ethyl acetate:hexane:methanol, 4.5:4.5:1)
  6. customFurther purification
  7. customOn evaporation
  8. customthe residue was triturated with cold diethyl ether

Sources & evidence

ORD record
ord-f06e732e7fc044cc8c9ccb4239b9f85c
Source dataset
uspto-grants-1986_11
Patent number
US04624961

Reaction notes

Loading…