Ethanol → 2-Chloro-3-fluoro-4-[4-(N-methyl-N-ethylcarbamoyl)phenylsulphanyl]aniline

HRID 2120378노트

반응식

HRID 2120378 반응식
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([S:9][C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:21])[N:17]([CH3:20])[CH2:18][CH3:19])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[N+:22]([O-])=O.CCO.O.C(=O)(O)[O-].[Na+]>Cl.[Fe].CCOC(C)=O>[Cl:1][C:2]1[C:7]([F:8])=[C:6]([S:9][C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:21])[N:17]([CH3:20])[CH2:18][CH3:19])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[NH2:22]

참가 물질

8

반응물 4

HCID 702EthanolHCID 962WaterHCID 516892Sodium BicarbonateHCID 234394082-Chloro-3-fluoro-4-[4-(N-methyl-N-ethylcarbamoyl)phenylsulphanyl]nitrobenzene

생성물 1

HCID 234394162-Chloro-3-fluoro-4-[4-(N-methyl-N-ethylcarbamoyl)phenylsulphanyl]aniline수율 100.6%

시약·촉매·용매 3

HCID 313Hydrochloric Acid촉매HCID 23925Iron촉매HCID 8857Ethyl Acetate용매

실험 절차

2-Chloro-3-fluoro-4-[4-(N-methyl-N-ethylcarbamoyl)phenylsulphanyl]nitrobenzene (Method 81; 650 mg. 1.76 mmol) was heated with stirring at 75° C. for 45 minutes with of iron powder (1.06 g), EtOH (1.2 ml), water (0.5 ml) and 2 drops of conc. HCl. The mixture was then allowed to cool to room temp, made basic with saturated sodium bicarbonate solution, and EtOAc was added. The reaction mixture was filtered through a bed of diatomaceous earth, washing through thoroughly with water and EtOAc. The organic layers were combined and washed with water, dried, filtered and evaporated to dryness to give the title compound (600 mg) as a pale yellow gum. NMR: 1.0 (s, 3H), 2.8 (s, 3H), 3.2 (d, 2H), 6.2 (s, 1H), 7.0 (m, 2H), 7.2 (m, 3H).

후처리

  1. additionwas added
  2. filtrationThe reaction mixture was filtered through a bed of diatomaceous earth
  3. washwashing through thoroughly with water and EtOAc
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated to dryness

출처 및 근거

ORD 기록
ord-a0cead772eab4c8e8b30feff7a0342c0
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06689909B1

반응 노트

불러오는 중…