Water → N-[3-[2-(4-fluorophenylthio)-6-fluorophenyl]prop-2-enyl]-O-tetrahydropyranyl hydroxylamine

HRID 1974760Notes

Reaction equation

HRID 1974760 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH2:8].[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=2[CH:24]=[CH:25][CH2:26]Br)=[CH:12][CH:11]=1.O.CCCCCC.C(OCC)(=O)C>CN(C=O)C>[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=2[CH:24]=[CH:25][CH2:26][NH:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 21226206Ethyl acetate hexaneHCID 540068731-[2-(4-Fluorophenylthio)-6-fluorophenyl]3-bromoprop-1-ene

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

O-tetrahydropyranylhydroxylamine (2.88 g, 24.6 mmol) is dissolved in 15 ml of dry DMF. A solution of 1-[2-(4-fluorophenylthio)-6-fluorophenyl]3-bromoprop-1-ene (2.80 g, 8.2 mmol) in 6 ml of DMF is added and the reaction is stirred for 4 hours at room temperature. The reaction mixture is poured into 200 ml of water and then extracted twice with diethyl ether. The extracts are washed three times with water and then with brine and dried over MgSO4 to afford the crude product. Chromatography on silica gel eluting with 5:1 hexane/ethyl acetate afforded the subtitle compound.

Workup

  1. extractionextracted twice with diethyl ether
  2. washThe extracts are washed three times with water
  3. dry with materialwith brine and dried over MgSO4
  4. customto afford the crude product

Sources & evidence

ORD record
ord-bdb257a1e95b4e1b90aaa522f3f6adef
Source dataset
uspto-grants-1994_02
Patent number
US05283361

Reaction notes

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