N-acetyl-o-toluidine → 3-Acetamido-4-methylbenzene-1-sulfonyl chloride

HRID 1672411

反応式

HRID 1672411 の反応式
[Cl:1][S:2]([OH:5])(=O)=[O:3].[C:6]([NH:9][C:10]1[C:11]([CH3:16])=[CH:12][CH:13]=[CH:14][CH:15]=1)(=[O:8])[CH3:7].COCC(NC1C=CC=CC=1)=O>C1C=CC=CC=1>[C:6]([NH:9][C:10]1[CH:15]=[C:14]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:13]=[CH:12][C:11]=1[CH3:16])(=[O:8])[CH3:7]

参加物

5

反応物 3

HCID 8443N-acetyl-o-toluidineHCID 24638Chlorosulfonic acidHCID 2642222-methoxy-N-phenylacetamide

生成物 1

HCID 545943883-Acetamido-4-methylbenzene-1-sulfonyl chloride

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

反応条件

温度
10 °C

実験手順

Chlorosulfonic acid (500 g.) was taken in a three neck round bottom flask equipped with a guard tube and cooled it to 10° C. N-acetyl 2-toluidine (100 g.) was added in small portions maintaining temperature below 10° C. After complete addition of 2-methoxy acetanilide cooling is removed and reaction was brought to 25° C. Reaction mixture was stirred at 25° C. for further 24 hours. After the completion of reaction (TLC), the reaction mixture was poured on ice-water, and the resulting slurry was filtered on buchner funnel. Solid cake on funnel was washed with 500 mL of water and the resulting solid was dried on phosphorus pentoxide in a desiccator to obtain 113.5 grams off white solid. It was found to contain a mixture of two isomers as confirmed from NMR and HPLC; however the desired isomer was obtained by partial crystallization using benzene and used for further experimentation, after the thorough carectorisation.

後処理

  1. customequipped with a guard tube
  2. temperaturemaintaining temperature below 10° C
  3. customis removed
  4. customreaction
  5. customwas brought to 25° C
  6. customReaction mixture
  7. customAfter the completion of reaction (TLC)
  8. additionthe reaction mixture was poured on ice-water
  9. filtrationthe resulting slurry was filtered on buchner funnel
  10. washSolid cake on funnel was washed with 500 mL of water
  11. customthe resulting solid was dried on phosphorus pentoxide in a desiccator
  12. customto obtain 113.5 grams off white solid
  13. additiona mixture of two isomers
  14. customhowever the desired isomer was obtained by partial crystallization

出典と根拠

ORDレコード
ord-93c966f566a443cc85f54105e5a872b4
出典データセット
uspto-grants-2011_08
特許番号
US07998981B2

関連ノート

読み込み中…