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

HRID 65176

반응식

HRID 65176 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7440c1c62ce147ae8b3c555fcbd6f3d9
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04613208

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