Sodium Iodide → 2-Chloro-4-nitro-4'-(4-heptyloxyphenyl)-azobenzene

HRID 65176

反応式

HRID 65176 の反応式
[Cl:1][C:2]1[CH2:7][C:6]([N+:15]([O-:17])=[O:16])(C2C=CC(O)=CC=2)[CH:5]=[CH:4][C:3]=1[N:18]=[N:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Br[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].[C:34](=[O:37])([O-])[O-].[K+].[K+].[I-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:4][C:3]=1[N:18]=[N:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[CH:7]=[CH:6][C:34]([O:37][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:4][CH:3]=2)=[CH:22][CH:21]=1

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 123691-BromoheptaneHCID 867410382-Chloro-4-nitro-4-(4-hydroxyphenyl)azobenzene

生成物 1

HCID 202333592-Chloro-4-nitro-4'-(4-heptyloxyphenyl)-azobenzene収率 104.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 1.3 g of crude 2-chloro-4-nitro-4-(4-hydroxyphenyl)azobenzene, 20 ml of ethanol, 0.658 g of 1-bromoheptane, 0.528 g of potassium carbonate and a spatula tip of sodium iodide was boiled at reflux while stirring for 22 hours. The brown suspension was subsequently concentrated in vacuo and the residue was chromatographed on silica gel with toluene/hexane as the eluent. Recrystallization from methylene chloride/hexane, yielded 0.863 g of 2-chloro-4-nitro-4'-(4-heptyloxyphenyl)-azobenzene as orange crystals; m.p. (C-N) 83.1°-83.7° C., cl.p. (N-I) 179.4°-179.8° C.; E300 =11580, E406 =25910.

後処理

  1. temperatureat reflux
  2. concentrationThe brown suspension was subsequently concentrated in vacuo
  3. customthe residue was chromatographed on silica gel with toluene/hexane as the eluent
  4. customRecrystallization from methylene chloride/hexane

出典と根拠

ORDレコード
ord-7440c1c62ce147ae8b3c555fcbd6f3d9
出典データセット
uspto-grants-1986_09
特許番号
US04613208

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