Chlorotrimethylsilane → HCID 5257301, compound

HRID 1074914Notes

Reaction equation

HRID 1074914 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.C(N(CC)CC)C.[CH3:16][Si:17]([CH3:20])([CH3:19])Cl>C1(C)C=CC=CC=1>[CH3:16][Si:17]([NH:7][C:3]1[CH:4]=[CH:5][CH:6]=[C:1]([NH:8][Si:17]([CH3:20])([CH3:19])[CH3:16])[CH:2]=1)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 7935M-PhenylenediamineHCID 8471Triethylamine

Product 1

HCID 5257301HCID 5257301, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

m-Phenylenediamine (10.8 g; 0.1 mole) and triethylamine (20.2 g; 0.2 mole) in dry toluene (100 ml) were stirred and treated with trimethylchlorosilane (21.7 g; 0.2 mole) which was added dropwise over 1 hour. Stirring was continued for a further hour, and the mixture was then heated under reflux for 1 hour. After cooling and filtering the product, the solvent was evaporated to leave 24.2 g of m-bis(trimethylsilylamino)benzene, which is hereinafter referred to as Silamine II. This product has a theoretical amino-hydrogen equivalent weight of 63, i.e., its theoretical amino-hydrogen content is 15.87 equivalents/kg.

Workup

  1. additionwas added dropwise over 1 hour
  2. waitwas continued for a further hour
  3. temperaturethe mixture was then heated
  4. temperatureunder reflux for 1 hour
  5. temperatureAfter cooling
  6. filtrationfiltering the product
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-49d7499295d24c258c6c10bd385dbdbc
Source dataset
uspto-grants-1983_07
Patent number
US04394492

Reaction notes

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