Triethylamine → HCID 19018149, compound

HRID 257124Notes

Reaction equation

HRID 257124 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][Si:11]([CH3:27])([CH3:26])[O:12][Si:13]([CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[OH:25])([CH3:15])[CH3:14].[N:28]#[C:29]Br.[CH2:31]([N:33](CC)CC)C>C(Cl)Cl>[O:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][CH2:17][CH2:16][Si:13]([CH3:14])([CH3:15])[O:12][Si:11]([CH2:10][CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][C:29]#[N:28])([CH3:27])[CH3:26])[C:31]#[N:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10476Cyanogen BromideHCID 22111943HCID 22111943, compound

Product 1

HCID 19018149HCID 19018149, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 750ml methylene chloride solution containing 40.2 g (0.1 mole) of 1,3-bis-(3'-(2-hydroxylphenyl)-propyl)-1,1,3,3-tetramethyldisiloxane from A above is added 25.42 g (0.24 mole, 97% purity) of cyanogen bromide (CNBr) at -30° C. and 26.31 g (0.26 mole, 98% purity) of triethylamine is then added at -30° C. in 15 minutes. An exothermic reaction is observed. After completion of addition, the reaction temperature is maintained at -25° C. to -15° C. for 30 minutes and -15° C. to -5° C. for 30 min. The mixture is then hydrolyzed with 150 ml H2O and washed once with 0.2N HCl and three times with 150 ml portions of H2O. The solution is dried over MGSO4, resulting in 45 g of a viscous liquid after stripping off solvent at <145° C./<10 mm Hg. The structure is confirmed by IR and 1H NMR. IR(neat): 3350cm-1 (aromatic hydroxyl disappeared), 2250 cm-1 (strong --CN); 1H NMR (CDCl3): 0 to 0.8 ppm (m, Si--CH3 and Si--CH2 --), 1.6-2.0 ppm (m, --CH2 --), 2.8 ppm (t, --CH2 --), 7.3-7.6 ppm (m, Ar--H).

Workup

  1. customAn exothermic reaction
  2. additionAfter completion of addition
  3. temperaturethe reaction temperature is maintained at -25° C. to -15° C. for 30 minutes and -15° C. to -5° C. for 30 min
  4. washhydrolyzed with 150 ml H2O and washed once with 0.2N HCl and three times with 150 ml portions of H2O
  5. customThe solution is dried over MGSO4

Sources & evidence

ORD record
ord-496328fdda6c4cbbb3097e1d6cba4583
Source dataset
uspto-grants-1993_11
Patent number
US05260398

Reaction notes

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