Trimethylsilyl isocyanate → HCID 54485360, compound

HRID 467140Notes

Reaction equation

HRID 467140 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([S:9][C:10]2[S:14][C:13]([CH2:15][CH2:16][NH:17][OH:18])=[CH:12][CH:11]=2)[CH:6]=[CH:7][CH:8]=1.C[Si]([N:25]=[C:26]=[O:27])(C)C>O1CCOCC1>[OH:18][N:17]([CH2:16][CH2:15][C:13]1[S:14][C:10]([S:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:19])[F:20])[CH:4]=2)=[CH:11][CH:12]=1)[C:26]([NH2:25])=[O:27]

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 54127079HCID 54127079, compound

Product 1

HCID 54485360HCID 54485360, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-[5-(3-trifluoromethylphenylthio)thien-2-ylethyl]hydroxylamine (7.6 g) in dioxan (70 ml) at room temperature under nitrogen, was added trimethylsilylisocyanate (5.48 g) and the reaction mixture stirred for 2 hours. The solution was quenched with saturated aqueous ammonium chloride, extracted with ether (2×100 ml), dried over MgSO4, 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, m.p. 124°-126° C.

Workup

  1. customThe solution was quenched 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, m.p. 124°-126° C.

Sources & evidence

ORD record
ord-d14ce0a2ca914bca8954ea96311b3a28
Source dataset
uspto-grants-1992_10
Patent number
US05158971

Reaction notes

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