Hydrochloric Acid → HCID 54212794, compound

HRID 467147Notes

Reaction equation

HRID 467147 reaction equation
[F:1][C:2]([F:17])([F:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[S:12][C:11]([CH2:13][NH:14][OH:15])=[CH:10][CH:9]=1.C[Si]([N:22]=[C:23]=[O:24])(C)C.Cl>O1CCOCC1>[OH:15][N:14]([CH2:13][C:11]1[S:12][C:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([F:1])([F:16])[F:17])=[CH:9][CH:10]=1)[C:23]([NH2:22])=[O:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 70696Trimethylsilyl isocyanateHCID 19813499HCID 19813499, compound

Product 1

HCID 54212794HCID 54212794, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-[5-(6,6,6-trifluorohexyl)thien-2-ylmethyl]hydroxylamine (1.4 g) in dioxan (50 ml) under nitrogen with stirring, was added trimethylsilyl isocyanate (1.42 ml) and the reaction mixture stirred for 1 hour, poured onto 2N hydrochloric acid (100 ml), extracted with ether (2×100 ml), dried over magnesium sulphate and evaporated under reduced pressure to give a pale yellow oil. The oil was flash chromatographed on a Sorbsil C60-40/60H column using 4:1 hexane/ethyl acetate to give a white solid. Recrystallised from ether/petroleum ether (40°-60° C.) to give a white crystlline solid m.p. 94° C.

Workup

  1. extractionextracted with ether (2×100 ml)
  2. dry with materialdried over magnesium sulphate
  3. customevaporated under reduced pressure
  4. customto give a pale 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-0b3f683eed914e0ba0e21547109cdf7c
Source dataset
uspto-grants-1992_10
Patent number
US05158971

Reaction notes

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