Triethylamine → 2,6-Dichloro-N-trimethylsilylaniline

HRID 359951Notes

Reaction equation

HRID 359951 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].C(N(CC)CC)C.[CH3:17][Si:18](Br)([CH3:20])[CH3:19]>C1C=CC=CC=1>[CH3:17][Si:18]([CH3:20])([CH3:19])[NH:4][C:3]1[C:2]([Cl:1])=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118462,6-DichloroanilineHCID 76113Bromotrimethylsilane

Product 1

HCID 143626792,6-Dichloro-N-trimethylsilylanilineYield 75.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 60 ml of benzene, 5.0 g (30.9 mmole) of 2,6-dichloroaniline, 10.6 ml (76.0 mmole) of triethylamine, and 8.08 ml (61.1 mmole) of trimethylsilyl bromide was heated at reflux for 54 hours, cooled, filtered, and the solvent was removed from the filtrate in vacuo. The residue was evacuated at 1 mm to remove any excess trimethylsilyl bromide. The residual mixture was filtered into a round-bottomed flask and distilled using a short Vigreaux column to provide 5.43 g (23.2 mmole, 75.0 percent yield) of the N-trimethylsilyl-2,6-dichloroaniline as a 97 percent pure amber oil, bp 74° C.-75° C. at 0.4 mm.

Workup

  1. temperatureat reflux for 54 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customthe solvent was removed from the filtrate in vacuo
  5. customThe residue was evacuated at 1 mm
  6. customto remove any excess trimethylsilyl bromide
  7. filtrationThe residual mixture was filtered into a round-bottomed flask
  8. distillationdistilled

Sources & evidence

ORD record
ord-977f491e642b43b79d611a9d7ec62df8
Source dataset
uspto-grants-1991_03
Patent number
US05003096

Reaction notes

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