Trimethylsilyl isocyanate → HCID 10826621, compound

HRID 467139Notes

Reaction equation

HRID 467139 reaction equation
[C:1]1([S:7][C:8]2[S:12][C:11]([CH2:13][NH:14][OH:15])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N:20]=[C:21]=[O:22])(C)C>O1CCOCC1>[OH:15][N:14]([CH2:13][C:11]1[S:12][C:8]([S:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:9][CH:10]=1)[C:21]([NH2:20])=[O:22]

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 10681371HCID 10681371, compound

Product 1

HCID 10826621HCID 10826621, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-(5-phenylthiothien-2-ylmethyl)-hydroxylamine (2.5 g) in dioxan (50 ml) at room temperature under nitrogen, was added trimethylsilylisocyanate (2.42 g) and the resulting solution stirred for 1 hour, quenched with saturated aqueous ammonium chloride, extracted with ether (2×100 ml), dried over MgSO4 and evaporated under reduced pressure to give a yellow oil. The oil was flash chromatographed on a Sorbsil C60-40/60H column using ether to give a white solid, recrystallised from ether/petroleum ether to give a white crystalline solid m.p. 127°-129° C.

Workup

  1. customquenched with saturated aqueous ammonium chloride
  2. extractionextracted with ether (2×100 ml)
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure
  5. customto give a yellow oil
  6. customchromatographed on a Sorbsil
  7. customto give a white solid
  8. customrecrystallised from ether/petroleum ether

Sources & evidence

ORD record
ord-30923bdff8954f2a931fbc132778f3d4
Source dataset
uspto-grants-1992_10
Patent number
US05158971

Reaction notes

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