Acetic Acid → HCID 23295917, compound

HRID 361498Notes

Reaction equation

HRID 361498 reaction equation
[OH:1][CH:2]([CH2:21]O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:19](=[O:20])[C:18]2[N:16]([CH3:17])[CH:15]=[N:14][C:13]=2[N:11]([CH3:12])[C:9]1=[O:10].[BrH:23].O.C(=O)(O)[O-].[Na+].[C:30]([OH:33])(=O)[CH3:31]>>[C:30]([O:1][CH:2]([CH2:21][Br:23])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:19](=[O:20])[C:18]2[N:16]([CH3:17])[CH:15]=[N:14][C:13]=2[N:11]([CH3:12])[C:9]1=[O:10])(=[O:33])[CH3:31]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 962WaterHCID 516892Sodium BicarbonateHCID 9818153HCID 9818153, compound

Product 1

HCID 23295917HCID 23295917, compoundYield 91%

Procedure

1-(6,7-Dihydroxyheptyl)-theobromine (4.00 g, 12.9 mmol) was stirred with hydrogen bromide (12.53 g of a 30% solution in acetic acid, 38.7 mmol) for 2 hours. The mixture was then added over 10 minutes to water (50 mL), ice (50 g) and sodium bicarbonate (30 g) and stirred for 30 minutes. The reaction mixture was extracted with dichloromethane (3×100 mL). A combined organic phase was dried over magnesium sulfate and the solvent was evaporated to obtain a residue (4.90 g, 91% yield) of 1-(6-acetoxy-7-bromoheptyl)-3,7-dimethylxanthine.

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane (3×100 mL)
  2. dry with materialA combined organic phase was dried over magnesium sulfate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-080bed5e6f194fd18949e968b5fc4d7a
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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