3-Chloro-2-nitroaniline → 3-(Methylthio)-2-nitroaniline

HRID 657520

反応式

HRID 657520 の反応式
Cl[C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH3:12][S-:13].[Na+]>CN(C=O)C>[CH3:12][S:13][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([NH2:5])[CH:6]=[CH:7][CH:8]=1

参加物

4

反応物 2

HCID 1010683-Chloro-2-nitroanilineHCID 4378561Sodium methanethiolate

生成物 1

HCID 109761553-(Methylthio)-2-nitroaniline収率 38.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

20 g of 3-chloro-2-nitroaniline are dissolved in 230 ml of dry DMF. The mixture was cooled to 0° C. and sodium methanethiolate (10 g) was added portionwise. The mixture was stirred for 2 h at 20° C. The solvent was evaporated in vacuo and the residue taken up in water and EA (200 ml each). The aqueous layer was extracted with EA, and the combined organic phases were washed with brine and dried over sodium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography (300 g silica gel; cyclohexane/EA, gradient from 100:0 to 50:50). 8.3 g of the title compound were obtained as a red solid.

後処理

  1. customThe solvent was evaporated in vacuo
  2. extractionThe aqueous layer was extracted with EA
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed in vacuo
  6. customThe crude product was purified by flash chromatography (300 g silica gel; cyclohexane/EA, gradient from 100:0 to 50:50)

出典と根拠

ORDレコード
ord-b0344d6bbcf34323b70aa3ba9e037cd7
出典データセット
uspto-grants-2011_12
特許番号
US08076324B2

関連ノート

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