Dimethylformamide → 4-Chloro-6-methoxy-7-[2-(1,2,3-triazol-1-yl)ethoxy]quinazoline

HRID 1597243Notes

Reaction equation

HRID 1597243 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]1[CH:20]=[CH:19][N:18]=[N:17]1)[N:9]=[CH:8][N:7]=[CH:6]2.CN(C=O)C.S(Cl)([Cl:28])=O>>[Cl:28][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][N:16]3[CH:20]=[CH:19][N:18]=[N:17]3)=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 216992806-Methoxy-7-(2-(1,2,3-triazol-1-yl)ethoxy)quinazoline

Product 1

HCID 108045444-Chloro-6-methoxy-7-[2-(1,2,3-triazol-1-yl)ethoxy]quinazolineYield 71%

Conditions

Temperature
80 °C

Procedure

A solution of 6-methoxy-7-(2-(1,2,3-triazol-1-yl)ethoxy)quinazoline (920 mg, 3.2 mmol) in thionyl chloride (10 ml) containing DMF (0.9 ml) was heated at 80° C. for 1 hour. After evaporation of the volatiles, the residue was azeotroped with toluene. The residue was partitioned between ethyl acetate and water and the aqueous layer was adjusted to pH8 with solid sodium hydrogen carbonate. The organic layer was washed with water, brine, dried (MgSO4), and the volatiles were removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (96/4) to give 4-chloro-6-methoxy-7-(2-(1,2,3-triazol-1-yl)ethoxy)quinazoline (693 mg, 71%).

Workup

  1. customAfter evaporation of the volatiles
  2. customthe residue was azeotroped with toluene
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customthe volatiles were removed by evaporation
  7. customThe residue was purified by column chromatography
  8. washeluting with methylene chloride/methanol (96/4)

Sources & evidence

ORD record
ord-f1f56740bfc34c548d06bcf59b145f14
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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