HCID 53889938, compound → HCID 72596483, compound

HRID 1019332Notes

Reaction equation

HRID 1019332 reaction equation
[CH3:1][O:2][C:3](=[O:15])[N:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]=O)[O:5][CH3:6].[CH3:16][O:17][N:18]=[C:19]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[C:20](=[N:22][NH2:23])[CH3:21]>CO>[CH3:1][O:2][C:3](=[O:15])[N:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]=[N:23][N:22]=[C:20]([CH3:21])[C:19](=[N:18][O:17][CH3:16])[C:24]1[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=1)[O:5][CH3:6]

Participants

4

Reactant 2

HCID 53889938HCID 53889938, compoundHCID 57321825HCID 57321825, compound

Product 1

HCID 72596483HCID 72596483, compoundYield 23.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.05 g of (2-formyl-phenyl)-N-methoxycarbamic acid methyl ester and 1.05 g of 1-(4-fluorophenyl)-2-hydrazono-propan-1-on-O-methyl-oxime in 5 ml of methanol is stirred at room temperature for 4 hours. The resulting by-product (symmetric azine of 1-(4-fluorophenyl)-2-hydrazono-propan-1-on-O-methyl-oxime) is removed by filtration and the filtrate is placed in a refrigerator over night. The product which has crystallised is filtered off (1.0 g). By concentrating the mother liquor and by means of fractional crystallisation of the residue, a further 0.48 g of the title compound are obtained in the form of yellow crystals having a melting point of 88-90° C.

Workup

  1. customThe resulting by-product (symmetric azine of 1-(4-fluorophenyl)-2-hydrazono-propan-1-on-O-methyl-oxime) is removed by filtration
  2. waitthe filtrate is placed in a refrigerator over night
  3. customThe product which has crystallised
  4. filtrationis filtered off (1.0 g)
  5. concentrationBy concentrating the mother liquor
  6. customby means of fractional crystallisation of the residue

Sources & evidence

ORD record
ord-1530460635a24b9185dbaed26806da53
Source dataset
uspto-grants-2002_11
Patent number
US06486341B1

Reaction notes

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