Hydrochloric Acid → N-(4-hydroxyphenyl)methanesulfonamide

HRID 1855316ノート

反応式

HRID 1855316 の反応式
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.[CH3:9][S:10](Cl)(=[O:12])=[O:11].O.Cl>N1C=CC=CC=1>[CH3:9][S:10]([NH:7][C:6]1[CH:5]=[CH:4][C:3]([OH:8])=[CH:2][CH:1]=1)(=[O:12])=[O:11]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 4034-AminophenolHCID 962WaterHCID 31297Methanesulfonyl chloride

生成物 1

HCID 4483147N-(4-hydroxyphenyl)methanesulfonamide収率 23.1%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒3 回

反応条件

温度
20 °C

実験手順

5.4 g (49.5 mmol) of p-aminophenol are dissolved in 40 ml of anhydrous pyridine, and 5.7 g (1 equivalent) of methanesulfonyl chloride diluted in 12 ml of pyridine are added over 15 minutes at 20° C. under a stream of nitrogen. The reaction medium is stirred for 3 days at 20° C. and is then poured into 1.5 liters of water containing a sufficient amount of hydrochloric acid (67 g of 36% HCl) to neutralize the pyridine and to establish a pH≦1.5. The aqueous phase is separated out by settling and extracted twice with 250 ml of ethyl acetate. The organic phases are combined and washed with twice 250 ml of water and then concentrated under vacuum. The residue is recrystallized from 40 ml of ethyl acetate. The crystals are filtered off at 0° C. and washed with 15 ml of ethyl acetate. 2.14 g of crude p-methanesulfonamidophenol are obtained.

後処理

  1. additionare added over 15 minutes at 20° C. under a stream of nitrogen
  2. customThe aqueous phase is separated out
  3. extractionextracted twice with 250 ml of ethyl acetate
  4. washwashed with twice 250 ml of water
  5. concentrationconcentrated under vacuum
  6. customThe residue is recrystallized from 40 ml of ethyl acetate
  7. filtrationThe crystals are filtered off at 0° C.
  8. washwashed with 15 ml of ethyl acetate

出典と根拠

ORDレコード
ord-2761cb5bfb5845edbd7a2286a5b6b4ec
出典データセット
uspto-grants-2015_02
特許番号
US08962869B2

反応ノート

読み込み中…