Triethylamine → HCID 10640011, compound

HRID 990581Notes

Reaction equation

HRID 990581 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH2:6].C(N(CC)CC)C.Cl[Si:18]([CH3:26])([CH3:25])[CH2:19][CH2:20][Si:21](Cl)([CH3:23])[CH3:22]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][N:6]1[Si:21]([CH3:23])([CH3:22])[CH2:20][CH2:19][Si:18]1([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 835521,2-Bis(chlorodimethylsilyl)ethaneHCID 457587Benzenemethanamine, 3-bromo-

Product 1

HCID 10640011HCID 10640011, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The conversion of Polymer 1 into Polymer 2 was preceded by the preparation of 1-(3-bromobenzyl)-2,2,5,5-tetramethyl-1,2,5-azadisilolidine. 3-Bromobenzylamine hydrochloride (25.0 g, 112.3 mmol) was converted to the free base by neutralization with sodium hydroxide and extraction into methylene chloride. Drying and solvent removal resulted in 20.3 g of a brown liquid which was used as such. To the above 3-bromobenzylamine (20.3 g, 109 mmol), in a round bottom flask equipped with a condenser and under argon atmosphere, was added 150 mL of methylene chloride and 30.3 mL (217 mmol) of triethylamine. To this stirred mixture cooled with an ice bath was added slowly 109 mL (109 mmol) of 1 M 1,2-bis(chlorodimethylsilyl)ethane dissolved in methylene chloride. During the addition, considerable precipitate formed. The ice-bath was removed and the mixture was stirred for another 6.5 h at room temperature. The white solid was removed by filtration and washed with methylene chloride (2×30 mL). The filtrate was evaporated using a rotary evaporator resulting in further precipitate formation. Hexanes (100 mL) were added to this mixture. The solid was removed by filtration and washed with hexanes (2×20 mL). After hexane removal from the filtrate, a yellowish liquid was obtained which was distilled to yield 29.0 g (82% yield) of light yellowish liquid (bp. 93-5° C./0.05 mm Hg).

Workup

  1. temperatureTo this stirred mixture cooled with an ice bath
  2. additionDuring the addition, considerable precipitate
  3. customformed
  4. customThe ice-bath was removed
  5. customThe white solid was removed by filtration
  6. washwashed with methylene chloride (2×30 mL)
  7. customThe filtrate was evaporated
  8. customa rotary evaporator
  9. customresulting in further precipitate formation
  10. customThe solid was removed by filtration
  11. washwashed with hexanes (2×20 mL)
  12. customAfter hexane removal from the filtrate
  13. customa yellowish liquid was obtained which
  14. distillationwas distilled
  15. customto yield 29.0 g (82% yield) of light yellowish liquid (bp. 93-5° C./0.05 mm Hg)

Sources & evidence

ORD record
ord-8b0808d0e9f24ced8f8d985ba64ccb29
Source dataset
uspto-grants-2002_10
Patent number
US06461585B1

Reaction notes

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