Sodium Hydroxide → HCID 58972455, compound

HRID 2264407Notes

Reaction equation

HRID 2264407 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[C:11]([O:15][CH3:16])[CH:10]=[C:9]2[C:4]=1[C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[N:6][C:7](O)=[N:8]2.P(Cl)(Cl)([Cl:26])=O.[OH-].[Na+]>>[Cl:26][C:7]1[N:6]=[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:4]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[C:12]([O:13][CH3:14])[C:3]=2[O:2][CH3:1])[N:8]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178486883HCID 178486883, compound

Product 1

HCID 58972455HCID 58972455, compoundYield 11.3%

Procedure

A solution of 5,6,7-trimethoxy-4-phenyl-quinazolin-2-ol (0.21 g, 0.67 mmol, 1.0 equiv) in phosphorus oxychloride (25.0 mL, 41.9 g, 273.1 mmol, 407.6 equiv) was heated to 110° C. for 1.5 h. The reaction mixture was poured on ice, the pH adjusted to 9 by addition of a 1 M solution of NaOH and the solution extracted with ethyl acetate (3×10 mL). The organic phase was dried over Na2SO4 and concentrated by evaporation under reduced pressure yielding 25.0 mg (11%) of the title compound which was used in the consecutive step without further purification. MS (ISP): 331.3 [M+H]+.

Workup

  1. additionThe reaction mixture was poured on ice
  2. extractionthe solution extracted with ethyl acetate (3×10 mL)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-3edf108fc0cb450799fe4114678b28b7
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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