Diisopropyl Ether → 4-(N-methylacetamido)benzene-1-sulfonyl chloride

HRID 260881

反応式

HRID 260881 の反応式
[CH3:1][N:2]([C:9](=[O:11])[CH3:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:12][S:13](O)(=[O:15])=[O:14].C(OC(C)C)(C)C>CCCCCC>[C:9]([N:2]([C:3]1[CH:8]=[CH:7][C:6]([S:13]([Cl:12])(=[O:15])=[O:14])=[CH:5][CH:4]=1)[CH3:1])(=[O:11])[CH3:10]

参加物

5

反応物 3

HCID 7914Diisopropyl EtherHCID 11364N-MethylacetanilideHCID 24638Chlorosulfonic acid2 回

生成物 1

HCID 2931464-(N-methylacetamido)benzene-1-sulfonyl chloride収率 42%

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
80 °C

実験手順

N-Methylacetanilide (25.0 g, 188.0 mmol) was added to chlorosulfonic acid (62.8 ml) under cooling with ice in portions at such a rate as not to raise the temperature of the resulting mixture to 50° C. or above, which took about 10 minutes. The obtained mixture was stirred at 80° C. for 2.5 hours and poured into a mixture comprising ice (200 ml), hexane (30 ml) and isopropyl ether (30 ml) under cooling with ice at 20° C. or below in portions to decompose excess chlorosulfonic acid. The precipitated crystal was recovered by filtration, washed with water and dissolved in ethyl acetate. The obtained solution was washed with water and a saturated aqueous solution of common salt. The organic layer was dried over magnesium sulfate and concentrated to give the title compound as a white crystal (19.4 g, yield: 42%).

後処理

  1. temperatureunder cooling with ice in portions at such a rate as not
  2. temperatureto raise the temperature of the resulting mixture to 50° C. or above
  3. temperatureunder cooling with ice at 20° C. or below in portions
  4. filtrationThe precipitated crystal was recovered by filtration
  5. washwashed with water
  6. dissolutiondissolved in ethyl acetate
  7. washThe obtained solution was washed with water
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-21aed41447f044a99ae1569d431f5828
出典データセット
uspto-grants-1996_06
特許番号
US05530118

関連ノート

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