Acetic Acid → HCID 23295940, compound

HRID 361550Notes

Reaction equation

HRID 361550 reaction equation
[OH:1][CH:2]([CH2:28]O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:24](=[O:25])[C:23]2[N:22]([CH3:26])[CH:21]=[N:20][C:19]=2[N:18]([CH3:27])[C:16]1=[O:17].[BrH:30].O.C([O-])(O)=O.[Na+].[C:37]([OH:40])(=O)[CH3:38]>>[C:37]([O:1][CH:2]([CH2:28][Br:30])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:24](=[O:25])[C:23]2[N:22]([CH3:26])[CH:21]=[N:20][C:19]=2[N:18]([CH3:27])[C:16]1=[O:17])(=[O:40])[CH3:38]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 962WaterHCID 516892Sodium BicarbonateHCID 23435624HCID 23435624, compound

Product 1

HCID 23295940HCID 23295940, compound

Procedure

1-(13,14-Dihydroxytetradecyl)-3,7-dimethylxanthine (0.80 g, 1.96 mmol) was stirred with HBr (1.94 mL of a 30% solution in acetic acid, 5.88 mmol) for 2 hours. The mixture was then added over 10 minutes to water (20 mL), ice (15 g) and NaHCO3 (3.5 g) and stirred for 30 minutes. The reaction mixture was extracted with dichloromethane (2×50 mL), the combined organic phases were dried using magnesium sulfate and the solvent was evaporated to obtain a residue of 1-(13-acetoxy-14-bromotetradecyl)-3,7-dimethylxanthine.

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane (2×50 mL)
  2. customthe combined organic phases were dried
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-37c97c09641142d381fffbddc976ab02
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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