Ammonium Chloride → HCID 53683307, compound

HRID 1974768Notes

Reaction equation

HRID 1974768 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH:15]=[CH:16][CH2:17][NH:18][OH:19])=[CH:4][CH:3]=1.C[Si]([N:24]=[C:25]=[O:26])(C)C.[NH4+].[Cl-]>O1CCOCC1>[OH:19][N:18]([CH2:17][CH:16]=[CH:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[S:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[C:25]([NH2:24])=[O:26]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 70696Trimethylsilyl isocyanateHCID 54383067HCID 54383067, compound

Product 1

HCID 53683307HCID 53683307, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To N-[3-[2-(4-fluorophenylthio)phenyl]prop-2-enyl]hydroxylamine (1.30 g; 4.7 mmol) in 24 ml of dry dioxane was added trimethylsilylisocyanate dropwise and the reaction mixture stirred at room temperature overnight. The mixture was poured into saturated NH4Cl and extracted twice with diethyl ether. The organics were combined, washed with 1N HCl and twice with water, and then brine, and dried over MgSO4. The solids were recrystallized from ethyl acetate and washed with cold diethyl ether to afford 0.76 g of the subtitle compound mp 124°-125° C.

Workup

  1. extractionextracted twice with diethyl ether
  2. washwashed with 1N HCl and twice with water
  3. dry with materialbrine, and dried over MgSO4
  4. customThe solids were recrystallized from ethyl acetate
  5. washwashed with cold diethyl ether

Sources & evidence

ORD record
ord-312034e1cdd449a1b62ce454206c096c
Source dataset
uspto-grants-1994_02
Patent number
US05283361

Reaction notes

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