Sodium Hydroxide → 5-Chlorosulphonyl-2-(4-ethylphenyl)thiophene

HRID 1067617ノート

反応式

HRID 1067617 の反応式
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([S:14](N3C=CC=C3)(=[O:16])=[O:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)[CH3:2].[OH-].[Na+].P(Cl)(Cl)([Cl:26])=O.P(Cl)(Cl)(Cl)(Cl)Cl>CO>[Cl:26][S:14]([C:12]1[S:13][C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)=[CH:10][CH:11]=1)(=[O:16])=[O:15]

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 23445382N-[5-(4-ethylphenyl)thiophene-2-sulfonyl]pyrrole

生成物 1

HCID 234455655-Chlorosulphonyl-2-(4-ethylphenyl)thiophene

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

A solution of N-[5-(4-ethylphenyl)thiophene-2-sulfonyl]pyrrole (100 mg, 0.32 mmol) and 6 N sodium hydroxide (1 mL) in methanol (1.5 ml) was refluxed for approximately 6 h. Evaporation of solvents and drying in vacuo resulted in an oil. Phosphorus oxychloride (258 ml, 2.52 mmol) and phosphorus pentachloride (131 mg, 0.63 mmol) were added to the oil and the resulting brown suspension was heated at 50° C. for 3 h. The resulting clear brown solution was carefully added to about 20 mL of crushed ice and then extracted with ethyl acetate (3×25 mL). The combined organic layers was washed with brine (2×5 mL), dried (MgSO4) and evaporated to leave an oily residue. Flash chromatography over silica gel using 2% ethyl acetate/hexanes yielded (53 mg, 59%) of the pure ulfonyl chloride as a pale yellow oil.

後処理

  1. customEvaporation of solvents
  2. customdrying in vacuo
  3. customresulted in an oil
  4. extractionextracted with ethyl acetate (3×25 mL)
  5. washThe combined organic layers was washed with brine (2×5 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto leave an oily residue

出典と根拠

ORDレコード
ord-7b81c7da9e024b2da2628722bad3792f
出典データセット
uspto-grants-2001_06
特許番号
US06248767B1

反応ノート

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