Chlorotrimethylsilane → 3,5-Dimethylaniline

HRID 1440009Notes

Reaction equation

HRID 1440009 reaction equation
C[Si](C)(C)Cl.[CH3:6][C:7]1[CH:8]=[C:9]([N:14]=C=O)[CH:10]=[C:11]([CH3:13])[CH:12]=1>>[CH3:6][C:7]1[CH:8]=[C:9]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[NH2:14]

Participants

3

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 5214883,5-Xylyl isocyanate

Product 1

HCID 79493,5-Dimethylaniline

Procedure

In order to improve the properties of the thus obtained Compound Bs3 as a separating agent for chromatography, the compound was subjected to a conventional end capping treatment with trimethylchlorosilane. The resulting product was collected by filtration with a G4 glass filter and the residue was washed as above with tetrahydrofuran, methanol, acetone and hexane, and then dried in vacuum at 60° C. for 2 hours, to obtain a product to be used as a separating agent for chromatography. The chiral resolution ability of the compound was investigated as a separating agent for various racemic compounds. Results obtained are shown in Table 2. 3,5-Dimethylphenyl isocyanate used above can be readily obtained from 3,5-dimethylaniline by using phosgene, triphosgene, or the like.

Workup

  1. filtrationThe resulting product was collected by filtration with a G4 glass
  2. filtrationfilter
  3. washthe residue was washed as above with tetrahydrofuran, methanol, acetone and hexane
  4. customdried in vacuum at 60° C. for 2 hours
  5. customto obtain a product
  6. customResults
  7. customobtained

Sources & evidence

ORD record
ord-60555e19ca3e4e48a23e793ba33c15aa
Source dataset
uspto-grants-1996_03
Patent number
US05496937

Reaction notes

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