Trityl chloride → (2-Bromoethyl)tritylamine

HRID 1526304Notes

Reaction equation

HRID 1526304 reaction equation
[Br:1][CH2:2][CH2:3][NH2:4].[C:5](Cl)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C>ClCCl>[Br:1][CH2:2][CH2:3][NH:4][C:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 78512-BromoethylamineHCID 8471Triethylamine

Product 1

HCID 15718287(2-Bromoethyl)tritylamineYield 62.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromoethanamine (5.00 g) and trityl chloride (6.80 g) in dichloromethane (24 mL) was slowly added triethylamine (7.48 mL) under ice-cooling, and the reaction mixture was stirred under ice-cooling for 2 hr. The resulting solid was removed by filtration, the filtrate was poured into water, and the mixture was extracted with dichloromethane. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from dichloromethane/cyclohexane to give the title compound (5.60 g).

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hr
  3. customThe resulting solid was removed by filtration
  4. additionthe filtrate was poured into water
  5. extractionthe mixture was extracted with dichloromethane
  6. washThe extract was washed with water and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was recrystallized from dichloromethane/cyclohexane

Sources & evidence

ORD record
ord-54f09493f98641baa9584f6120bbf75e
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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