Toluene → HCID 21478529, compound

HRID 2292506Notes

Reaction equation

HRID 2292506 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9](O)[C:8]1=[O:18])[CH3:2].C1(C)C=CC=CC=1.S(Cl)([Cl:28])=O>CN(C)C=O>[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([Cl:28])[C:8]1=[O:18])[CH3:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 178467832HCID 178467832, compound

Product 1

HCID 21478529HCID 21478529, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 22.5 g of (1), 330 ml of toluene, 10 ml of dimethylformamide and 10 ml of thionyl chloride are added and the resulting mixture is heated to reflux for 2 hours. The mixture is then subjected to filtration during hot and the filtrate is concentrated. The resultant is purified by silica gel column chromatography (ethyl acetate:hexane=1:3-1:2) to obtain 23.5 g of (2) in the form of yellow oil.

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureto reflux for 2 hours
  3. filtrationThe mixture is then subjected to filtration during hot and the filtrate
  4. concentrationis concentrated
  5. customThe resultant is purified by silica gel column chromatography (ethyl acetate:hexane=1:3-1:2)

Sources & evidence

ORD record
ord-f4af5638634c4e159c73010c2ed2e687
Source dataset
uspto-grants-1997_11
Patent number
US05683998

Reaction notes

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