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

HRID 1974761Notes

Reaction equation

HRID 1974761 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][O:20]C2CCCCO2)=[CH:4][CH:3]=1.Cl>CO>[F:1][C:2]1[CH:3]=[CH:4][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:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54561379N-[3-[2-(4-fluorophenylthio)-6-fluorophenyl]prop-2-enyl]-O-tetrahydropyranyl hydroxylamine

Product 1

HCID 53877237N-[3-[2-(4-fluorophenylthio)-6-fluorophenyl]prop-2-enyl]hydroxylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[3-[2-(4-fluorophenylthio)-6-fluorophenyl]prop-2-enyl]-O-tetrahydropyranyl hydroxylamine (1.26 g, 3.34 mmol) is dissolved in 17 ml of methanol and cooled in an ice bath. Concentrated HCl (1.7 ml) is then added dropwise and the reaction mixture is stirred overnight at room temperature. The reaction mixture is evaporated to dryness and then slurried in saturated NaHCO3 solution and extracted twice with diethyl ether. The extracts are washed with water and then brine and dried over K2CO3 to afford the subtitle compound.

Workup

  1. temperaturecooled in an ice bath
  2. customThe reaction mixture is evaporated to dryness
  3. extractionextracted twice with diethyl ether
  4. washThe extracts are washed with water
  5. dry with materialbrine and dried over K2CO3

Sources & evidence

ORD record
ord-112f0cc4e1cc4a1c8e8186e9d47957e2
Source dataset
uspto-grants-1994_02
Patent number
US05283361

Reaction notes

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