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

HRID 2120378ノート

反応式

HRID 2120378 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid触媒HCID 23925Iron触媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a0cead772eab4c8e8b30feff7a0342c0
出典データセット
uspto-grants-2004_02
特許番号
US06689909B1

反応ノート

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