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

HRID 2372203ノート

反応式

HRID 2372203 の反応式
[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

参加物

5

反応物 3

HCID 69366Chloromethyl acetateHCID 5360545SodiumHCID 178467406HCID 178467406、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-57c3b15bf10941a1915f900f2dc53bc6
出典データセット
uspto-grants-1992_03
特許番号
US05098466

反応ノート

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