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

HRID 2372203노트

반응식

HRID 2372203 반응식
[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

참가 물질

5

반응물 3

HCID 69366Chloromethyl acetateHCID 5360545SodiumHCID 178467406HCID 178467406, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-57c3b15bf10941a1915f900f2dc53bc6
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05098466

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