Sodium Hydroxide → HCID 22031051, compound

HRID 1792494Notes

Reaction equation

HRID 1792494 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[C:12]1[S:16][C:15]([CH:17]=[O:18])=[CH:14][CH:13]=1.[OH-:19].[Na+]>O.CS(C)=O.[N+]([O-])([O-])=O.[Ag+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[C:12]1[S:16][C:15]([C:17]([OH:19])=[O:18])=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 22031755HCID 22031755, compound

Product 1

HCID 22031051HCID 22031051, compoundYield 82.6%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

A solution of 2.19 g silver nitrate in 40 mL water and a solution of 1.96 g 5-(6-bromoquinazolin-4-yl)thiophen-2-carboaldehyde (compound in Production Example 381) in 20 mL dimethyl sulfoxide were added little by little successively to a solution of 1.0 g sodium hydroxide in 40 mL water under ice-cooling, and the mixture was stirred at room temperature for 24 hours. The reaction solution was filtered through Celite and acidified with hydrochloric acid, and the precipitated crystals were filtered. This product was recrystallized from dichloromethane/methanol/ether, to give 1.7 g of the title compound as pale yellow crystals.

Workup

  1. temperaturecooling
  2. filtrationThe reaction solution was filtered through Celite
  3. filtrationthe precipitated crystals were filtered
  4. customThis product was recrystallized from dichloromethane/methanol/ether

Sources & evidence

ORD record
ord-9130d476b2234cf9a01bb669ea3c511b
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

Loading…