Dimethylamine → HCID 15766962, compound

HRID 1492138Notes

Reaction equation

HRID 1492138 reaction equation
[CH3:1][NH:2][CH3:3].Cl[C:5]1[C:14]2[C:9](=[C:10]([OH:15])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][N:6]=1>ClCCl>[CH3:1][N:2]([CH3:3])[C:5]1[C:14]2[C:9](=[C:10]([OH:15])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 157669614-Chloroquinazolin-8-ol

Product 1

HCID 15766962HCID 15766962, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethylamine gas is bubbled slowly through a solution of 4-chloro-8-quinazolinol (0.7 g, 3.88 mmol) in dichloromethane, under a nitrogen atmosphere, at 3° C. for 20 minutes. The cooling bath is removed and dimethylamine gas is bubbled through the reaction mixture for an additional 30 minutes. The reaction mixture is then concentrated in vacuo to obtain a grey solid. The solid is washed with water and extracted with 10% sodium hydroxide solution. The combined extracts are acidified to pH 7.0 and extracted with dichloromethane. The organic extracts are combined, dried over MgSO4 and concentrated in vacuo to give the title product as a grey solid, 0.36 g, mp 104°-105° C.

Workup

  1. customThe cooling bath is removed
  2. customdimethylamine gas is bubbled through the reaction mixture for an additional 30 minutes
  3. concentrationThe reaction mixture is then concentrated in vacuo
  4. customto obtain a grey solid
  5. washThe solid is washed with water
  6. extractionextracted with 10% sodium hydroxide solution
  7. extractionextracted with dichloromethane
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-db00309607164c8a931238780436c25b
Source dataset
uspto-grants-1994_12
Patent number
US05373011

Reaction notes

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