Water → HCID 53881546, compound

HRID 1974766Notes

Reaction equation

HRID 1974766 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]=[CH:19][C:18]=2[CH:23]=[CH:24][CH2:25]Br)=[CH:12][CH:11]=1.O>CN(C)C=O>[F:9][C:10]1[CH:11]=[CH:12][C:13]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH:23]=[CH:24][CH2:25][NH:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 54130451HCID 54130451, compound

Product 1

HCID 53881546HCID 53881546, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To O-tetrahydropyranyl hydroxylamine (2.77 g; 23.6 mmol) in 10 ml of dry dimethylformamide was added 1-[2-(4-fluorophenylthio)phenyl]-3-bromoprop-1-ene (2.54 g; 7.87 mmol) in 10 ml of dimethylformamide dropwise. The reaction mixture was stirred overnight at room temperature. The mixture was poured into 200 ml of water and extracted twice with diethyl ether. The organics were collected, washed twice with water and then with brine, dried over K2CO3 and concentrated. The crude subtitle compound was chromatographed by HPLC using 3:1 hexane/ethyl acetate and then 2:1 hexane/ethyl acetate to afford the subtitle compound.

Workup

  1. extractionextracted twice with diethyl ether
  2. customThe organics were collected
  3. washwashed twice with water
  4. dry with materialwith brine, dried over K2CO3
  5. concentrationconcentrated
  6. customThe crude subtitle compound was chromatographed by HPLC

Sources & evidence

ORD record
ord-b5d191dabd874866bcfe2934382b01d9
Source dataset
uspto-grants-1994_02
Patent number
US05283361

Reaction notes

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