Acetic Acid → HCID 23295917, compound

HRID 1954112Notes

Reaction equation

HRID 1954112 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-6c378f412c9e44c0b00bd23883a77b33
Source dataset
uspto-grants-2000_09
Patent number
US06121270

Reaction notes

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