Triethylamine → HCID 22161303, compound

HRID 1088594Notes

Reaction equation

HRID 1088594 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([N:13]=[N:14][C:15]2[CH:29]=[CH:28][C:18]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=O)=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].S(Cl)(Cl)=O.C(N(CC)CC)C.[CH3:41][CH2:42][O:43][Si:44]([O:52][CH2:53][CH3:54])([O:49][CH2:50][CH3:51])[CH2:45][CH2:46][CH2:47][NH2:48]>CCOCC>[CH2:50]([O:49][Si:44]([O:52][CH2:53][CH3:54])([O:43][CH2:42][CH3:41])[CH2:45][CH2:46][CH2:47][NH:48][C:25](=[O:27])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][O:19][C:18]1[CH:17]=[CH:16][C:15]([N:14]=[N:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:8][CH:9]=2)=[CH:29][CH:28]=1)[CH3:51]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13521(3-Aminopropyl)triethoxysilaneHCID 24386Thionyl Chloride2×HCID 19091976134509-34-5

Product 1

HCID 22161303HCID 22161303, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

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. temperaturewas refluxed for 2 hours
  2. temperatureThis mixture kept cooled with ice
  3. filtrationfiltered
  4. distillationsubjected to vacuum distillation at room temperature

Sources & evidence

ORD record
ord-3f42c7f3f5b54e77bac02e909ffdab7a
Source dataset
uspto-grants-1990_10
Patent number
US04963448

Reaction notes

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