Triethylamine → HCID 19018149, compound

HRID 1728433Notes

Reaction equation

HRID 1728433 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 750 ml 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): 3350 cm-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 p pm(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. dry with materialThe solution is dried over MgSO4

Sources & evidence

ORD record
ord-e368e51fcdf74af58f5def423ba659e4
Source dataset
uspto-grants-1994_07
Patent number
US05326893

Reaction notes

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