Tyramine → HCID 13298155, compound

HRID 66082Notes

Reaction equation

HRID 66082 reaction equation
[O:1]1[CH2:5]CCC1.[NH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.[CH3:16][Si:17]([CH3:20])([CH3:19])Cl>C(N(CC)CC)C>[CH3:16][Si:17]([CH3:20])([CH3:19])[O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][N:6]=[C:5]=[O:1])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 5610TyramineHCID 6397ChlorotrimethylsilaneHCID 8028Tetrahydrofuran

Product 1

HCID 13298155HCID 13298155, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Into a 250 ml, three-necked flask fitted with a reflux condenser, gas inlet tube and magnetic stirrer and kept under a positive pressure of dry nitrogen, there was charged 100 ml of dry tetrahydrofuran, 1.4g (0.01 mol) of tyramine and 5.0 ml of triethylamine. 3.0 ml of trimethylchlorosilane was then added at ambient temperature, dropwise and with stirring over a period of 30 minutes. Carbon dioxide was thereafter slowly bubbled into the reaction mixture, via a syringe needle for 4 hours while the mixture was allowed to reflux for the same period. Introduction of carbon dioxide was then terminated, and 1.5 ml of silicon tetrachloride was added slowly using a syringe. After 30 minutes of additional heating, the reaction mixture was allowed to cool, and triethylamine hydrochloride was removed by filtration. The solvent was then removed at 35° C. in vacuo (12 torr), and the resulting oil distilled at 88°-90° C. (0.05 torr) to give 2-(4'-trimethylsiloxyphenyl)ethyl isocyanate as a colorless liquid.

Workup

  1. customInto a 250 ml, three-necked flask fitted with a reflux condenser, gas inlet tube and magnetic stirrer
  2. customCarbon dioxide was thereafter slowly bubbled into the reaction mixture, via a syringe needle for 4 hours while the mixture
  3. temperatureto reflux for the same period
  4. customIntroduction of carbon dioxide was then terminated
  5. addition1.5 ml of silicon tetrachloride was added slowly
  6. waitAfter 30 minutes of additional heating
  7. temperatureto cool
  8. customtriethylamine hydrochloride was removed by filtration
  9. customThe solvent was then removed at 35° C. in vacuo (12 torr)
  10. distillationthe resulting oil distilled at 88°-90° C. (0.05 torr)

Sources & evidence

ORD record
ord-c0f5204db6344ff193d16f56f13db620
Source dataset
uspto-grants-1978_12
Patent number
US04130576

Reaction notes

Loading…