Chlorotrimethylsilane → 126101-07-3

HRID 344749Notes

Reaction equation

HRID 344749 reaction equation
[C:1]([C:4]1([CH2:10][CH2:11][C:12]([OH:14])=O)[NH:8][C:7](=[O:9])[CH2:6][NH:5]1)([OH:3])=[O:2].C[Si](C)(C)N[Si](C)(C)C.C[Si](C)(C)Cl>C(#N)C>[O:9]=[C:7]1[CH2:6][N:5]2[C:12](=[O:14])[CH2:11][CH2:10][C:4]2([C:1]([OH:3])=[O:2])[NH:8]1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 13838HexamethyldisilazaneHCID 10442822HCID 10442822, compound

Product 1

HCID 3079593126101-07-3Yield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-carboxy-4-oxo-2-imidazolidine-propanoic acid (2 g, 9.89 mmol), hexamethyldisilazane (20 mol) and trimethylchlorosilane (10 ml) in dry acetonitrile (50 ml) was refluxed under nitrogen for 4 hours. After cooling, the precipitate was filtered off and the filtrate was evaporated under vacuum. The residue was dissolved in methanol (20 ml) containing some drops of concentrated hydrochloric acid and stirred for 10 minutes. The insoluble material was filtered off and the filtrate was evaporated to dryness. The residue was triturated with acetonitrile and crystallized with tetrahydrofuran (250 ml) to yield 0.9 g (50%) of the title compound, m.p. 207° C. (with decomposition). NMR (DMSO-d6): deltaH : 9.20 (b.s., 1H, NH); 3.82 and 3.46 (ABq, J=16.8 Hz, 2H, NCH2CO); 2.90-1.80 (c.a., 4H, CH2 -CH2). MS (E.I., 70 eV, 1.5 mA) m/z=184 (M+), 139 (M--COOH)+, 83 (C3H3N2O)30 .

Workup

  1. temperaturewas refluxed under nitrogen for 4 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitate was filtered off
  4. customthe filtrate was evaporated under vacuum
  5. dissolutionThe residue was dissolved in methanol (20 ml)
  6. additioncontaining some drops of concentrated hydrochloric acid
  7. filtrationThe insoluble material was filtered off
  8. customthe filtrate was evaporated to dryness
  9. customThe residue was triturated with acetonitrile
  10. customcrystallized with tetrahydrofuran (250 ml)

Sources & evidence

ORD record
ord-085058b5d9f0410f8c1aa352ddff2c38
Source dataset
uspto-grants-1991_10
Patent number
US05053422

Reaction notes

Loading…