Dimethylformamide → HCID 17985343, compound

HRID 751495Notes

Reaction equation

HRID 751495 reaction equation
C[N:2](C)[CH:3]=[CH:4][C:5]1[C:13]2[O:12][CH:11]=[CH:10][C:9]=2[C:8]([N+:14]([O-:16])=[O:15])=[CH:7][CH:6]=1.NOS(O)(=O)=O.CN(C)C=O>C(OCC)C>[N+:14]([C:8]1[C:9]2[CH:10]=[CH:11][O:12][C:13]=2[C:5]([CH2:4][C:3]#[N:2])=[CH:6][CH:7]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 76284hydroxylamine-O-sulfonic acidHCID 85866839HCID 85866839, compound

Product 1

HCID 17985343HCID 17985343, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Add dimethyl[2-(4-nitrobenzofur-7-yl)vinyl]amine (4.8 g, 20.6 mmol) and hydroxylamine-O-sulfonic acid (4.6 g, 40.6 mmol) to dimethylformamide (45 mL) and stir at room temperature for 15 minutes. Heat at 100° C. under nitrogen for 1 hour, cool to room temperature, dilute with diethyl ether, and wash with water and aqueous saturated sodium chloride. Dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Chromatography on flash silica using 85% hexane, 15% ethyl acetate gives 2.9 g (64%) of the title compound as a light brown solid. Mass spectrum (ES, m/z) (M−1)=200.9.

Workup

  1. temperatureHeat at 100° C. under nitrogen for 1 hour
  2. temperaturecool to room temperature
  3. washwash with water and aqueous saturated sodium chloride
  4. dry with materialDry over anhydrous magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-1052d80f493e4e1b900d03cf7db53cba
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

Loading…