Ethanol → HCID 178513359, compound

HRID 1791349Notes

Reaction equation

HRID 1791349 reaction equation
C(O)C.[S:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]#[N:10].Cl.[NH2:12][OH:13].[OH-].[Na+]>ClCCl.O>[OH:13][NH:12][C:9]([C:5]1[S:4][CH:8]=[CH:7][CH:6]=1)=[NH:10]

Participants

7

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 660872-ThiophenecarbonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 178513359HCID 178513359, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To an ethanol (5 mL) solution of 2-thiophenecarbonitrile (525.5 mg, 5 mmol), 5 M hydroxylamine hydrochloride (1.1 mL) and 1 M sodium hydroxide (5.5 mL) were added. After the reaction mixture was heated at 80° C. for 3 h, water and dichloromethane were added. The organic layer was dried, concentrated and triturated with hexanes to give a white solid 625.8 mg (88%). 1H NMR (DMSO-d6), δ(ppm): 9.6 (s, 1H), 7.46 (m, 2H), 7.05 (t, 1H), 5.93 (bs, 2H).

Workup

  1. customThe organic layer was dried
  2. concentrationconcentrated
  3. customtriturated with hexanes

Sources & evidence

ORD record
ord-a9abdd14d13e4aaab88e0d197f3e87dd
Source dataset
uspto-grants-2006_07
Patent number
US07074809B2

Reaction notes

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