Water → HCID 22504373, compound

HRID 1814135Notes

Reaction equation

HRID 1814135 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[C:9][CH2:10][OH:11])=[N:6][C:5]([S:12][CH3:13])=[CH:4][N:3]=1.O>CN(C)C=O.[Cu]I>[CH3:13][S:12][C:5]1[N:6]=[C:7]2[CH:8]=[C:9]([CH2:10][OH:11])[NH:1][C:2]2=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 962WaterHCID 22504411HCID 22504411, compound

Product 1

HCID 22504373HCID 22504373, compoundYield 40.7%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of the compound obtained in Example 34 (3) (381 mg) in N,N-dimethylformamide (10 ml), copper(I) iodide (111 mg) was added and the mixture was stirred at 150° C. for 2 hours. The reaction solution was poured into water, and the mixture was extracted with chloroform, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was separated using silica gel preparative thin-layer chromatography (chloroform:methanol=20:1) to obtain 155 mg (40.7%) of the desired product as a yellow powder.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was separated

Sources & evidence

ORD record
ord-9871dd32efaf4821b4d71480fa3c6c7d
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

Loading…