Sodium → 134509-34-5

HRID 1088593Notes

Reaction equation

HRID 1088593 reaction equation
[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]

Participants

7

Reactant 4

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 22161301Oxan-2-yl 6-bromohexanoateHCID 13570282833228-49-8

Product 1

HCID 19091976134509-34-5Yield 68.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-823c726ce50549ccbd7892827ed846b0
Source dataset
uspto-grants-1990_10
Patent number
US04963448

Reaction notes

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