Carbon Dioxide → HCID 13178323、化合物

HRID 1074372ノート

反応式

HRID 1074372 の反応式
[C:1]([NH:5][S:6]([C:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[S:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[C:23](=[O:25])=[O:24].Cl>CCCCCC.O.O1CCCC1>[C:1]([NH:5][S:6]([C:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[S:11][C:10]=1[C:23]([OH:25])=[O:24])(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

8

反応物 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 13178322N-tert-Butylbenzothiophene-3-sulfonamideHCID 178418339Butyllithium

生成物 1

HCID 13178323HCID 13178323、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

N-tert-Butylbenzothiophene-3-sulfonamide (13.6 g) and 400 ml of anhydrous tetrahydrofuran in admixture were cooled to 0° and 120 ml of butyl lithium in hexane (1.6 molar) was added cautiously, dropwise. After the addition was completed the mixture was stirred at room temperature for 2 hours and carbon dioxide was then passed into the system for two hours while cooling to 15°. Two hundred ml of water was then cautiously added followed by 40 ml of 12 N hydrochloric acid. The solution was then evaporated to half of its original volume, extracted with methylene chloride and the organic phase washed with water, dried over magnesium sulfate, filtered and evaporated to dryness to yield a white solid of m.p. 180° with gas evolution. Nuclear Magnetic Resonance spectroscopy showed the t-butyl absorption at 1.3 δ (singlet) and benzothiophene hydrogen absorption at 7.4-8.0 (multiplet).

後処理

  1. additionAfter the addition
  2. temperaturewhile cooling to 15°
  3. customThe solution was then evaporated to half of its original volume
  4. extractionextracted with methylene chloride
  5. washthe organic phase washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customto yield a white solid of m.p. 180° with gas evolution
  10. customthe t-butyl absorption
  11. customat 1.3 δ (singlet) and benzothiophene hydrogen absorption at 7.4-8.0 (multiplet)

出典と根拠

ORDレコード
ord-49d017ebe778494d85f4e8a9edaa4829
出典データセット
uspto-grants-1983_07
特許番号
US04391627

反応ノート

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