Chlorotrimethylsilane → HCID 53984494, compound

HRID 466590Notes

Reaction equation

HRID 466590 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]=[O:11])=[CH:5][N:4]=1.[CH3:12][Si:13](Cl)([CH3:15])[CH3:14].C(N(CC)CC)C>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH:10]=[O:11])[Si:13]([CH3:15])([CH3:14])[CH3:12])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 19814509HCID 19814509, compound

Product 1

HCID 53984494HCID 53984494, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
10 °C

Procedure

N-(2-Methoxy-5-pyridyl)formamide (30.4 g, 0.2 mol) was added to 200 ml benzene. This was stirred with a mechanical stirrer under argon at 10° C. Trimethylsilyl chloride (25 g, 0.23 mol) was added. While stirring at 10° C., triethylamine (21 g, 0.21 mol) dissolved in 50 ml benzene was added dropwise over 0.5 hour. The slurry was warmed to room temperature and after 0.5 hour filtered. The salt cake was washed with 100 ml benzene and the combined filtrates concentrated on a rotary evaporator at 30° C. under aspirator vacuum. The dark liquid product was distilled under reduced pressure. A clear liquid, 39 g, 87% yield, (b.p. 87° C./0.25 mmHg). The product was stored under argon.

Workup

  1. stirringWhile stirring at 10° C.
  2. additionwas added dropwise over 0.5 hour
  3. temperatureThe slurry was warmed to room temperature and after 0.5 hour
  4. filtrationfiltered
  5. washThe salt cake was washed with 100 ml benzene
  6. concentrationthe combined filtrates concentrated on a rotary evaporator at 30° C. under aspirator vacuum
  7. distillationThe dark liquid product was distilled under reduced pressure

Sources & evidence

ORD record
ord-0bff61b89b6d483d86bef7f2b936d5fd
Source dataset
uspto-grants-1992_10
Patent number
US05157043

Reaction notes

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