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Sodium → 134509-34-5

HRID 1088593
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HRID 1088593 반응식
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([N:13]=[N:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Na].C[O-].[Na+].Br[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34]C1CCCCO1)=[O:33]>O.CC(N(C)C)=O>[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([N:13]=[N:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]
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참가 물질

7

반응물 4

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 22161301Oxan-2-YL 6-bromohexanoateHCID 1357028284-[2-(4-Hexylphenyl)hydrazinylidene]cyclohexa-2,5-dien-1-one

생성물 1

HCID 19091976134509-34-5수율 68.3%

시약·촉매·용매 2

HCID 962Water
용매
HCID 31374Dimethylacetamide용매

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온도
100 °C

실험 절차

One g. (3.73×10-3 mol) of 4'-hexyl-4-hydroxyazobenzene (1) converted into a sodium salt with sodium methylate and 1.03 g (3.69×10-3 mol) of 2-tetrahydropyranyl 6-bromohexanoate and 5 ml of dimethylacetamide added thereto were heated for reaction at 100° C. for 73 hours. After the reaction was completed, the reaction mixture was diluted with water and left to cool to room temperature. The yellow crystals which were consequently precipitated were separated by filtration. The crystals were extracted with ethyl acetate, dried with magnesium sulfate, and subjected to vacuum distillation for expulsion of the solvent. The residue of the vacuum distillation was recrystallized with a mixture of hexane with benzene. Consequently, 1 g of 6-[4-(4-hexylphenylazo)-phenoxy]-hexanoic acid was obtained. A mixture of 200 mg (5.05×10-4 mol) of this carboxylic acid with 5 ml of thionyl chloride was refluxed for 2 hours to expel excess thionyl chloride and then mixed with 3 ml of dry ether and 0.15 g (1.485×10-3 mol) of triethylamine. This mixture kept cooled with ice and a solution of 0.11 g (4.98×10-4 mol) of triethoxyaminopropylsilane in 3 ml of dry ether added dropwise thereto were stirred for two hours, then filtered to expel the formed salt in an atmosphere of nitrogen gas, and subjected to vacuum distillation at room temperature to expel the solvent. Consequently, 213 mg of yellow waxy N-(3-triethoxysilylpropyl)-6-[4-(4-hexylphenylazo)phenoxy]hexanoic acid amide was obtained.

후처리

  1. additionadded
  2. waitleft
  3. temperatureto cool to room temperature
  4. customThe yellow crystals which were consequently precipitated
  5. customwere separated by filtration
  6. extractionThe crystals were extracted with ethyl acetate
  7. dry with materialdried with magnesium sulfate
  8. distillationsubjected to vacuum distillation for expulsion of the solvent
  9. distillationThe residue of the vacuum distillation
  10. customwas recrystallized with a mixture of hexane with benzene

출처 및 근거

ORD 기록
ord-823c726ce50549ccbd7892827ed846b0
출처 데이터셋
uspto-grants-1990_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04963448

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