Isothiocyanatotrimethylsilane → HCID 54253279, compound

HRID 467141Notes

Reaction equation

HRID 467141 reaction equation
[CH2:1]([S:6][C:7]1[S:11][C:10]([CH2:12][NH:13][OH:14])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C[Si]([N:19]=[C:20]=[S:21])(C)C>O1CCOCC1>[OH:14][N:13]([CH2:12][C:10]1[S:11][C:7]([S:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:8][CH:9]=1)[C:20]([NH2:19])=[S:21]

Participants

4

Reactant 2

HCID 75297IsothiocyanatotrimethylsilaneHCID 19813491HCID 19813491, compound

Product 1

HCID 54253279HCID 54253279, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-[5-n-pentylthiothien-2-ylmethyl]-hydroxylamine (4.36 g) in dioxan (60 ml) at room temperature under nitrogen, was added trimethylsilylisothiocyanate (3.11 g) and the solution heated at reflux for 1 hour. The cooled solution was quenched with saturated aqueous ammonium chloride, dried over MgSO4 and evaporated under reduced pressure to give a brown oil. The oil was flash chromatographed on a Sorbsil C60-40/60H column using ether to give a pale yellow solid, recrystallized from n-hexane to give a cream crystalline solid m.p. 112°-114° C.

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux for 1 hour
  3. customThe cooled solution was quenched with saturated aqueous ammonium chloride
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customto give a brown oil
  7. customchromatographed on a Sorbsil
  8. customto give a pale yellow solid
  9. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-499424d923e74cae823c88984c16a4e0
Source dataset
uspto-grants-1992_10
Patent number
US05158971

Reaction notes

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