Chlorotrimethylsilane → HCID 20349900, compound

HRID 1449111Notes

Reaction equation

HRID 1449111 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[C:18]2[C:17](=[O:19])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:20])[C:9]=2[C:8]([NH:21][CH2:22][CH2:23][OH:24])=[CH:7][CH:6]=1.C(N(CC)CC)C.[CH3:32][Si:33]([CH3:36])([CH3:35])Cl>O1CCCC1>[CH3:32][Si:33]([CH3:36])([CH3:35])[O:24][CH2:23][CH2:22][NH:21][C:8]1[C:9]2[C:10](=[O:20])[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17](=[O:19])[C:18]=2[C:5]([NH:4][CH2:3][CH2:2][O:1][Si:33]([CH3:36])([CH3:35])[CH3:32])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 20549C.I. Disperse Blue 23

Product 1

HCID 20349900HCID 20349900, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a flame dried 250 ml, three-necked flask equipped with magnetic stirring bar, reflux condenser with nitrogen inlet and rubber septum on one side neck, are placed 1.63 g (5.0 mmol) 1,4-bis(2-hydroxyethylamino)anthraquinone (C.I. Disperse Blue 23, available as Disperse Blue NSP from Inmont Corporation), 4 ml triethylamine and 50 ml tetrahydrofurane (THF) (Aldrich, freshly opened). The mixture is purged with nitrogen and stirred until the dye is at least partially dissolved and 1.55 ml (12 mmol) trimethylchlorosilane is added to the mixture during a two minute period by means of a syringe having its needle through the septum. A mild exothermic reaction occurs and a precipitate forms immediately. The color of the mixture remains deep blue throughout the reaction. After stirring overnight, the reaction mixture is filtered and the whitish solid (triethylamine hydrochloride) washed with fresh THF until it remains white. The filtrate is evaporated on a rotary evaporator and the residue recrystallized from hot hexane. 1,4-Bis(2-trimethylsilyloxyethylamino)anthraquinone is obtained in two crops of blue needles in 86% yield, m.p. 123°-126° C.

Workup

  1. customIn a flame dried 250 ml, three-necked flask
  2. customequipped with magnetic stirring bar
  3. temperaturereflux condenser with nitrogen inlet
  4. customThe mixture is purged with nitrogen
  5. dissolutionpartially dissolved
  6. customA mild exothermic reaction
  7. customThe color of the mixture remains deep blue throughout the reaction
  8. stirringAfter stirring overnight
  9. filtrationthe reaction mixture is filtered
  10. washthe whitish solid (triethylamine hydrochloride) washed with fresh THF until it
  11. customThe filtrate is evaporated on a rotary evaporator
  12. customthe residue recrystallized from hot hexane

Sources & evidence

ORD record
ord-814f4e29d1f644ceab2b94162b4e8a6a
Source dataset
uspto-grants-1980_02
Patent number
US04189429

Reaction notes

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