Hydrochloric Acid → N-hydroxy-N-[3-[2-(4-fluorophenylthio)-6-fluorophenyl]prop-2-enyl]urea

HRID 1974762Notes

Reaction equation

HRID 1974762 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:10]=2[CH:16]=[CH:17][CH2:18][NH:19][OH:20])=[CH:4][CH:3]=1.C[Si]([N:25]=[C:26]=[O:27])(C)C.Cl>O1CCOCC1>[OH:20][N:19]([CH2:18][CH:17]=[CH:16][C:10]1[C:11]([F:15])=[CH:12][CH:13]=[CH:14][C:9]=1[S:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[C:26]([NH2:25])=[O:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 70696Trimethylsilyl isocyanateHCID 53877237N-[3-[2-(4-fluorophenylthio)-6-fluorophenyl]prop-2-enyl]hydroxylamine

Product 1

HCID 54054261N-hydroxy-N-[3-[2-(4-fluorophenylthio)-6-fluorophenyl]prop-2-enyl]urea

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-[3-[2-(4-fluorophenylthio)-6-fluorophenyl]prop-2-enyl]hydroxylamine (0.91 g, 3.1 mmol) is dissolved in 16 ml of dry dioxane. Trimethylsilyl isocyanate (0.36 g, 3.1 mmol) is then added dropwise and the reaction mixture is stirred at room temperature overnight. The reaction mixture is poured into 1N HCl solution and then extracted twice with diethyl ether. The extracts are washed with water and then with brine and dried over K2CO3 to afford the crude product. Recrystallization from ethyl acetate afforded the subtitle compound.

Workup

  1. extractionextracted twice with diethyl ether
  2. washThe extracts are washed with water
  3. dry with materialwith brine and dried over K2CO3
  4. customto afford the crude product
  5. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-e8a00009d2e14fceb9c1b9cccd241fb8
Source dataset
uspto-grants-1994_02
Patent number
US05283361

Reaction notes

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