Sodium Hydroxide → HCID 178433176, compound

HRID 505336Notes

Reaction equation

HRID 505336 reaction equation
I.[Cl:2][C:3]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]2[C:4]=1[CH:5]([CH3:16])[NH:6][C:7](SC)=[N:8]2.[O:17]([CH2:24][CH2:25][NH2:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[Na+]>C(#N)C.OO.O>[Cl:2][C:3]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]2[C:4]=1[CH:5]([CH3:16])[NH:6][C:7]([NH:26][CH2:25][CH2:24][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[N:8]2

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 156512-PhenoxyethanamineHCID 178503353HCID 178503353, compound

Product 1

HCID 178433176HCID 178433176, compoundYield 93.3%

Reagents, catalysts & solvents 3

HCID 784Hydrogen PeroxideCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
170 °C

Procedure

5,8-Dichloro-4-methyl-2-methylsulfanyl-3,4-dihydro-quinazoline hydroiodide (116 mg, 0.30 mmol) and 2-phenoxyethyl amine (126 mg, 0.9 mmol) were dissolved in acetonitrile (0.9 ml) and heated to 170° C. in a sealed tube in a microwave oven for 30 minutes. After cooling the reaction was treated with 1N aqueous sodium hydroxide solution (0.9 ml) and 5 to 7 drops of 30% aqueous hydrogen peroxide solution. The reaction was diluted with water and the product precipitated as a white solid, which was filtered off, washed with water and dried in vacuo to yield the title compound (98 mg, 93%).

Workup

  1. temperatureAfter cooling the reaction
  2. customthe product precipitated as a white solid, which
  3. filtrationwas filtered off
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-70f8fd58311848c5b90c29af7bd968f6
Source dataset
uspto-grants-2010_08
Patent number
US07781441B2

Reaction notes

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