Potassium Hydroxide → N,N-Diethyl-3-hydroxy-4-amino-1-naphthalenesulfonamide

HRID 1034337

反応式

HRID 1034337 の反応式
[CH2:1]([N:3]([CH2:26][CH3:27])[S:4]([C:7]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:10]2[N:11]=C(C3C=CC=CC=3)[O:13][C:9]=2[CH:8]=1)(=[O:6])=[O:5])[CH3:2].[OH-].[K+]>C(O)C>[CH2:26]([N:3]([CH2:1][CH3:2])[S:4]([C:7]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:10]([NH2:11])=[C:9]([OH:13])[CH:8]=1)(=[O:6])=[O:5])[CH3:27]

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 3715238N,N-Diethyl-2-phenylnaphtho[1,2-d][1,3]oxazole-5-sulfonamide

生成物 1

HCID 9971689N,N-Diethyl-3-hydroxy-4-amino-1-naphthalenesulfonamide収率 154.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of N,N-diethyl-2-phenylnaphth[1,2-d]oxazole-5-sulfonamide (38.1 g, 100 mmol), 20% KOH (140 ml) and ethanol (180 ml) was refluxed for 24 h under nitrogen and the product was extracted with ethyl acetate (3×500 ml). The combined extracts were dried over anhydrous sodium sulfate and the solvent evaporated to give 45.4 g crude N,N-diethyl-4-amino-3-hydroxy-1-naphthalenesulfonamide as a black sticky oil (50% pure by NMR). An analytical sample was prepared by column chromatography (chloroform) to give pure N,N-diethyl-4-amino-3-hydroxy-1-naphthalenesulfonamide as a glassy material which upon trituration with ether gave a black solid, m.p. 120°-122° C.

後処理

  1. temperaturewas refluxed for 24 h under nitrogen
  2. extractionthe product was extracted with ethyl acetate (3×500 ml)
  3. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  4. customthe solvent evaporated

出典と根拠

ORDレコード
ord-029b2ddab4604ea28c30360825584374
出典データセット
uspto-grants-1994_05
特許番号
US05314998

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