Triethylamine → N-trimethylsilyl-2,6-dichloro-3-methylaniline

HRID 1165544Notes

Reaction equation

HRID 1165544 reaction equation
[Cl:1][C:2]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([Cl:10])[C:3]=1[NH2:4].[CH3:11][Si:12](Br)([CH3:14])[CH3:13].C(N(CC)CC)C>C1C=CC=CC=1>[CH3:11][Si:12]([CH3:14])([CH3:13])[NH:4][C:3]1[C:5]([Cl:10])=[CH:6][CH:7]=[C:8]([CH3:9])[C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76113BromotrimethylsilaneHCID 1165292,6-Dichloro-3-methylaniline

Product 1

HCID 11128643N-trimethylsilyl-2,6-dichloro-3-methylanilineYield 73.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 50 ml of benzene, 4.0 g (22.7 mmole) of 2,6-dichloro-3-methylaniline, 10.67 ml (80.8 mmole) of trimethylsilyl bromide, and 13.1 ml (94.0 mmole) of triethylamine was heated at reflux over 42 hours. The product was isolated as described in Example 1 to provide 4.14 g (16.7 mmole, 73.5 percent yield) of 98.0 percent pure N-trimethylsilyl-2,6-dichloro-3-methylaniline as a light yellow oil, b.p. 64°-68° C. at 0.03 mm.

Workup

  1. temperatureat reflux over 42 hours
  2. customThe product was isolated

Sources & evidence

ORD record
ord-ac2053fed34048bf849b87c13384a95b
Source dataset
uspto-grants-1990_03
Patent number
US04910306

Reaction notes

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