Chloromethyl acetate → Acetyloxymethyl 2-acetylnicotinate 4-(3-fluorophenyl)semicarbazone

HRID 2372203

Reaction equation

HRID 2372203 reaction equation
[Na].[F:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:24])[NH:11][N:12]=[C:13]([OH:23])[C:14]2[CH:19]=[CH:18][CH:17]=[N:16][C:15]=2[C:20](=[O:22])[CH3:21])[CH:6]=[CH:7][CH:8]=1.[C:25]([O:28][CH2:29]Cl)(=[O:27])[CH3:26]>CN(C=O)C>[F:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:24])[NH:11][N:12]=[C:13]([O:23][CH2:29][O:28][C:25](=[O:27])[CH3:26])[C:14]2[CH:19]=[CH:18][CH:17]=[N:16][C:15]=2[C:20](=[O:22])[CH3:21])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 69366Chloromethyl acetateHCID 5360545SodiumHCID 178467406HCID 178467406, compound

Product 1

HCID 67895779Acetyloxymethyl 2-acetylnicotinate 4-(3-fluorophenyl)semicarbazone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the sodium salt of compound 4 (1.0 g, 3.0 mmol) and chloromethyl acetate (0.4 g, 3.5 mmol) in 18 ml of DMF is stirred at RT for 3 days. The reaction mixture is poured onto ice. The solid which precipitates is collected by filtration, is washed with water and is air-dried. It is stirred in 50 ml of chloroform for 2 hours and is filtered. The filtrate is evaporated to give glass-like material, which is triturated with ether to give the crude product. Purification by prep. TLC gives acetyloxymethyl 2-acetylnicotinate 4-(3-fluorophenyl)semicarbazone, m.p. 159°-160° (compound 54, Table C).

Workup

  1. additionThe reaction mixture is poured onto ice
  2. customThe solid which precipitates
  3. filtrationis collected by filtration
  4. washis washed with water
  5. customis air-dried
  6. stirringIt is stirred in 50 ml of chloroform for 2 hours
  7. filtrationis filtered
  8. customThe filtrate is evaporated
  9. customto give glass-like material, which
  10. customis triturated with ether
  11. customto give the crude product
  12. customPurification by prep

Sources & evidence

ORD record
ord-57c3b15bf10941a1915f900f2dc53bc6
Source dataset
uspto-grants-1992_03
Patent number
US05098466

Linked notes

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