Ammonium Chloride → HCID 10805252, compound

HRID 467144Notes

Reaction equation

HRID 467144 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[S:13][C:12]([CH2:14][NH:15][OH:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C[Si]([N:21]=[C:22]=[O:23])(C)C.[Cl-].[NH4+]>O1CCOCC1>[OH:16][N:15]([CH2:14][C:12]1[S:13][C:9]([S:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[CH:10][CH:11]=1)[C:22]([NH2:21])=[O:23]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 70696Trimethylsilyl isocyanateHCID 10754617HCID 10754617, compound

Product 1

HCID 10805252HCID 10805252, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-[5-(4-chlorophenylthio)thien-2-ylmethyl]hydroxylamine (6.65 g) in dioxan (100 ml) at room temperature under nitrogen, was added trimethylsilylisocyanate (4.25 g) and the resulting solution stirred for 2 hours, poured onto 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 (40°-60° C.) to give a white crystalline solid m.p. 158°-160° C.

Workup

  1. extractionextracted with ether (2×100 ml)
  2. dry with materialdried over MgSO4
  3. customevaporated under reduced pressure
  4. customto give a yellow oil
  5. customchromatographed on a Sorbsil
  6. customto give a white solid
  7. customRecrystallised from ether/petroleum ether (40°-60° C.)

Sources & evidence

ORD record
ord-973cb313a2dc41c9a10c8aef4a4a5758
Source dataset
uspto-grants-1992_10
Patent number
US05158971

Reaction notes

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