Butyl isocyanate → 2-(Chloromethyl)-N-(butylaminocarbonyl)benzenesulfonamide

HRID 1153869

反応式

HRID 1153869 の反応式
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH2:12])(=[O:11])=[O:10].[CH2:13]([N:17]=[C:18]=[O:19])[CH2:14][CH2:15][CH3:16]>C1(C)C(C)=CC=CC=1.N12CCC(CC1)CN2>[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH:12][C:18]([NH:17][CH2:13][CH2:14][CH2:15][CH3:16])=[O:19])(=[O:11])=[O:10]

参加物

5

反応物 2

HCID 8110Butyl isocyanateHCID 133646272-(Chloromethyl)benzenesulfonamide

生成物 1

HCID 136318872-(Chloromethyl)-N-(butylaminocarbonyl)benzenesulfonamide収率 74.8%

試薬・触媒・溶媒 2

HCID 136165Diazabicyclo(2.2.2)octane触媒HCID 7237O-Xylene溶媒

実験手順

A mixture of 2-(chloromethyl)benzenesulfonamide (13.2 g, 64 mmol) and butyl isocyanate (7.0 g, 71 mmol) in xylene (80 ml) was contacted with diazabicyclo[2.2.2]-octane (0.25 g) and heated to reflux for 5.0 hrs. Volatiles were removed under vacuum and the residue was treated with 0.5N NaOH (200 ml) and extracted with ethyl acetate (75 ml). The aqueous layer was separated, chilled, acidified (pH 4) with hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated to give 14.6 g of white solid. A sample was recrystallized from toluene to give m.p. 104°-106°. 1H nmr δCDCl3TMS 9.5-8.1 (brds), 8.05-7.10 (m), 6.28 (t, J=2 Hz), 4.91 (s), 3.25-2.95 (m), 1.70-0.70 (m).

後処理

  1. temperatureheated
  2. temperatureto reflux for 5.0 hrs
  3. customVolatiles were removed under vacuum
  4. additionthe residue was treated with 0.5N NaOH (200 ml)
  5. extractionextracted with ethyl acetate (75 ml)
  6. customThe aqueous layer was separated
  7. temperaturechilled
  8. extractionextracted with ethyl acetate
  9. washThe organic layer was washed with brine
  10. dry with materialdried (MgSO4)
  11. customevaporated

出典と根拠

ORDレコード
ord-10390e26897849d38b250841db16aacf
出典データセット
uspto-grants-1984_12
特許番号
US04486589

関連ノート

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