Ammonium Chloride → 3-(Methylsulphonyl)aniline

HRID 341753

反応式

HRID 341753 の反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[CH:6]=1)(=[O:4])=[O:3].[Cl-].[NH4+]>C(O)C.O>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[CH:6]=1)(=[O:3])=[O:4]

参加物

4

反応物 2

HCID 25517Ammonium ChlorideHCID 763121-(Methylsulfonyl)-3-nitrobenzene

生成物 1

HCID 4280293-(Methylsulphonyl)aniline収率 85.5%

試薬・触媒・溶媒 1

HCID 19096565Water ethanol溶媒

実験手順

(3-Nitro)phenyl methyl sulphone (prepared as described in Step 1 above) (5.396 g) reduced iron (7.5 g) and ammonium chloride (7.18 g) were mixed together in ethanol/water (2:1) (150 ml) and heated under reflux for 2 hours. The black solution was filtered through `Celite` and the pad washed with ethyl acetate. The solvents were removed under reduced pressure and the residue taken up in ethyl acetate/water. The organic layer was separated and the aqueous layer extracted with 3 further portions of ethyl acetate. The combined organic layers were washed with brine and the solvent removed under reduced pressure to give a dark orange oil (3.9275 g). This was chromatographed on silica gel using ethyl acetate-hexane (45:55 to 50:50) as eluant to give the title compound as an orange oil, yield 3.607 g.

後処理

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. filtrationThe black solution was filtered through `Celite` and the pad
  4. washwashed with ethyl acetate
  5. customThe solvents were removed under reduced pressure
  6. customThe organic layer was separated
  7. extractionthe aqueous layer extracted with 3 further portions of ethyl acetate
  8. washThe combined organic layers were washed with brine
  9. customthe solvent removed under reduced pressure

出典と根拠

ORDレコード
ord-468b3da800a94e858c6b6de404755328
出典データセット
uspto-grants-1999_01
特許番号
US05856273

関連ノート

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