Theobromine → HCID 20041114, compound

HRID 1762551Notes

Reaction equation

HRID 1762551 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([CH3:11])[C:6]=2[C:5](=[O:12])[NH:4][C:3]1=[O:13].Cl[CH2:15][CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([CH3:11])[C:6]=2[C:5](=[O:12])[N:4]([CH2:15][CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[C:3]1=[O:13]

Participants

5

Reactant 3

HCID 5429TheobromineHCID 11430Potassium CarbonateHCID 133573926-Chloro-2-methylhex-2-ene

Product 1

HCID 20041114HCID 20041114, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.0 g (0.05 mol) of 3,7-dimethylxanthine, 8.0 g (0.06 mol) of 1-chloro-5-methyl-4-hexene and 8.3 g (0.06 mol) of potassium carbonate are stirred in 200 ml of dimethylformamide at 110° C. for 22 hours. After the solvent has been removed in vacuo, 100 ml of 1N sodium hydroxide solution are added and the mixture is extracted thoroughly with methylene chloride. The extract is extracted again by shaking with dilute sodium hydroxide solution, washed with water until neutral, dried and evaporated under reduced pressure and the residue is recrystallized from diisopropyl ether.

Workup

  1. customAfter the solvent has been removed in vacuo, 100 ml of 1N sodium hydroxide solution
  2. additionare added
  3. extractionthe mixture is extracted thoroughly with methylene chloride
  4. extractionThe extract is extracted again
  5. washwashed with water until neutral,
  6. customdried
  7. customevaporated under reduced pressure
  8. customthe residue is recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-52f373a3bdbb44d9b9796d537f485edf
Source dataset
uspto-grants-1989_05
Patent number
US04833146

Reaction notes

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