Chlorotrimethylsilane → 1-(2,2-Diethoxyethyl)-3-trimethylsilylcarbodiimide

HRID 464481Notes

Reaction equation

HRID 464481 reaction equation
[CH2:1]([O:3][CH:4]([O:9][CH2:10][CH3:11])[CH2:5][NH:6][C:7]#[N:8])[CH3:2].C(N(CC)CC)C.[CH3:19][Si:20](Cl)([CH3:22])[CH3:21]>C1COCC1>[CH2:1]([O:3][CH:4]([O:9][CH2:10][CH3:11])[CH2:5][N:6]=[C:7]=[N:8][Si:20]([CH3:22])([CH3:21])[CH3:19])[CH3:2]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 133930082,2-Diethoxyethylcyanamide

Product 1

HCID 135569311-(2,2-Diethoxyethyl)-3-trimethylsilylcarbodiimide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,2-diethoxyethylcyanamide (5.5 g.) in anhydrous THF (100 ml.) at 0° was added triethylamine (6.29 ml.) and trimethylsilyl chloride (5.73 ml.). The reaction mixture was stirred at room temperature for 3 hours, the precipitated triethylamine hydrochloride removed by filtration under nitrogen and the filtrate concentrated. The residue was taken up in CCl4, the solvent evaporated and the residue was distilled at 80°/0.2 mm to give 1-(2,2-diethoxyethyl)-3-trimethylsilylcarbodiimide (6.5 g.) having the following n.m.r. in CDCl3 : 0.219 (s, 9H); 1.244 (t, 6H); 3.256 (d, 2H); 3.486-3.798 (m, 4H); 4.55 (t, 1H).

Workup

  1. customthe precipitated triethylamine hydrochloride removed by filtration under nitrogen
  2. concentrationthe filtrate concentrated
  3. customthe solvent evaporated
  4. distillationthe residue was distilled at 80°/0.2 mm

Sources & evidence

ORD record
ord-4a275a08c6df4a8cad21bb20a86dc484
Source dataset
uspto-grants-1985_10
Patent number
US04547573

Reaction notes

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