Imidazole → HCID 20190090, compound

HRID 1788679Notes

Reaction equation

HRID 1788679 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][NH:6][C:5]1=[O:9].N1C=CN=C1.[C:15]([Si:19](Cl)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:18])([CH3:17])[CH3:16].C(OCC)C>CN(C)C=O.O.C(OCC)(=O)C>[Si:19]([O:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][NH:6][C:5]1=[O:9])([C:15]([CH3:18])([CH3:17])[CH3:16])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 77290Hydroxyethyl imidazolidinoneHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 20190090HCID 20190090, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(2-hydroxyethyl)-2-oxoimidazolidine (13 g) in dimethylformamide (50 ml) containing imidazole (7.5 g) was treated with t-butylchlorodiphenylsilane (28.6 ml) and the clear solution stirred for 3 hours at ambient temperature. The white suspension formed was dissolved in water (200 ml) and ethyl acetate (500 ml). The aqueous phase was re-extracted with ethyl acetate (100 ml) and the combined organic phases were washed with 3×100 ml portions of water, 1×100 ml brine, dried and evaporated to give a solid. Trituration of the solid with diethyl ether (100 ml) afforded the title compound as a white solid, (33.7 g).

Workup

  1. customThe white suspension formed
  2. extractionThe aqueous phase was re-extracted with ethyl acetate (100 ml)
  3. washthe combined organic phases were washed with 3×100 ml portions of water, 1×100 ml brine
  4. customdried
  5. customevaporated
  6. customto give a solid

Sources & evidence

ORD record
ord-2145a2297f49479d9a15bdbfa4ad4a3f
Source dataset
uspto-grants-1987_08
Patent number
US04684641

Reaction notes

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