Acetic Acid → HCID 23295940, compound

HRID 1954164Notes

Reaction equation

HRID 1954164 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-ae051f5a8b584c099af62376fb3b4fb1
Source dataset
uspto-grants-2000_09
Patent number
US06121270

Reaction notes

Loading…