Dimethylformamide → HCID 86667411, compound

HRID 1429086Notes

Reaction equation

HRID 1429086 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11](O)=[N:12][C:13]2[C:18]([N:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.S(Cl)([Cl:23])=O.CN(C=O)C>C1(C)C=CC=CC=1>[Cl:23][C:11]1[C:10]([C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)=[N:19][C:18]2[C:13]([N:12]=1)=[CH:14][CH:15]=[CH:16][CH:17]=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178517136HCID 178517136, compound

Product 1

HCID 86667411HCID 86667411, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 3-(benzo[d]thiazol-2-yl)quinoxalin-2-ol (251 mg, 0.900 mmol) in toluene (4500 μl) was added thionyl chloride (131 μl, 1.800 mmol) followed by DMF (69.7 μl, 0.900 mmol). The green mixture was stirred at 110° C. for 3 hr. The reaction mixture was evaporated under reduced pressure and the resulting solid was diluted with CHCl3 (30-40 ml) and the insoluble solid filtered and rinsed with CHCl3. The filtrate was evaporated under reduced pressure and the residue purified by flash chromatography on silica gel (eluted with chloroform, then dichloromethane) to provide the title compound as a light yellow solid.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. additionthe resulting solid was diluted with CHCl3 (30-40 ml)
  3. filtrationthe insoluble solid filtered
  4. washrinsed with CHCl3
  5. customThe filtrate was evaporated under reduced pressure
  6. customthe residue purified by flash chromatography on silica gel (
  7. washeluted with chloroform

Sources & evidence

ORD record
ord-37b0ba459d02465681b8ac025471e30f
Source dataset
uspto-grants-2015_01
Patent number
US08937041B2

Reaction notes

Loading…