Chlorotrimethylsilane → HCID 14278942, compound

HRID 2292336Notes

Reaction equation

HRID 2292336 reaction equation
[CH3:1][Si:2](Cl)([CH3:4])[CH3:3].[C:6]([O:10][C:11]([NH:13][N:14]1[CH2:18][CH2:17][NH:16][C:15]1=[O:19])=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>C(OCC)(=O)C>[C:6]([O:10][C:11]([NH:13][N:14]1[CH2:18][CH2:17][N:16]([Si:2]([CH3:4])([CH3:3])[CH3:1])[C:15]1=[O:19])=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 142789411-[(t-Butoxycarbonyl)amino]-2-imidazolidinone

Product 1

HCID 14278942HCID 14278942, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

While cooling, 10.55 g (97.1 mmol) of trimethylsilylchloride was dropped into a solution of 19.55 g (97.1 mmol) of 1-[(t-butoxycarbonyl)amino]-2-imidazolidinone and 9.83 g (97.1 mmol) of triethylamine in 900 ml of absolute ethyl acetate. After stirring overnight, the salt was filtered off and the filtrate evaporated in vacuo to yield 24.18 g of 1-[(t-butoxycarbonyl)amino]-3-(trimethylsilyl)-2-imidazolidinone, melting point 132.1° C.

Workup

  1. temperatureWhile cooling
  2. filtrationthe salt was filtered off
  3. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-d4d6516c83a74d83b9625255e9abb7ab
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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