Sodium Hydroxide → HCID 13298149, compound

HRID 1706374Notes

Reaction equation

HRID 1706374 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[C:5](=[O:11])[NH:4][C:3]1=[O:12].[OH-].[Na+].Br[CH2:16][CH2:17][CH:18]=[CH2:19]>CO.O>[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:19][CH2:18][CH:17]=[CH2:16])[C:6]=2[C:5](=[O:11])[NH:4][C:3]1=[O:12]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21241Homoallyl bromideHCID 706393-Methylxanthine

Product 1

HCID 13298149HCID 13298149, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

41.5 g of 3-methyl-xanthine are added with stirring at 70° C. to a solution of 10.2 g of NaOH in 400 ml of methanol/water (1:1). After mixing with 35.1 g of 4-bromobut-1-ene the mixture is stirred under a nitrogen atmosphere for 27 hours at 70° C. The reaction mixture is then cooled to 20° C. and the precipitate formed is filtered off. By re-precipitation from alkaline solution (pH 13.5) and acidification with dilute sulphuric acid to pH 10, 29.6 g (89.7% of theory relative to reacted 3-methyl-xanthine) of the title compound of melting point 245° to 246° C. are obtained after drying.

Workup

  1. temperatureThe reaction mixture is then cooled to 20° C.
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. customBy re-precipitation from alkaline solution (pH 13.5) and acidification with dilute sulphuric acid
  5. customto pH 10, 29.6 g (89.7% of theory relative to reacted 3-methyl-xanthine) of the title compound of melting point 245° to 246° C.
  6. customare obtained
  7. customafter drying

Sources & evidence

ORD record
ord-6735627665dc46b8ba6531aa743edf87
Source dataset
uspto-grants-1980_06
Patent number
US04207321

Reaction notes

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