Iodine → HCID 23295948, compound

HRID 361548Notes

Reaction equation

HRID 361548 reaction equation
[Mg].II.[CH2:4](Br)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[CH2:14].Br[CH2:17][CH2:18][CH2:19][Cl:20].S(=O)(=O)(O)O>C1COCC1.[Cu](I)I>[CH2:19]([Cl:20])[CH2:18][CH2:17][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=[CH2:4]

Participants

8

Reactant 5

HCID 807IodineHCID 1118Sulfuric AcidHCID 80061-Bromo-3-chloropropaneHCID 28414811-Bromo-1-undeceneHCID 5462224Magnesium

Product 1

HCID 23295948HCID 23295948, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

This example illustrates a synthesis of 1-(13,14-Oxidotetradecyl)-3,7-dimethylxanthine (inventive compound no. 3503). To a suspension of magnesium (1.86 g, 77.2 mmol) and a crystal of iodine in THF (20 mL) was added 10-undecenyl bromide (6.00 g, 25.8 mmol) in THF (14 mL) over 40 minutes and the reaction stirred for a further 30 minutes after the addition was complete. The solution was added via a canula over 50 minutes to a suspension of copper iodide (0.50 g, 2.58 mmol) and 1-bromo-3-chloropropane (3.84 mL, 38.7 mmol) in THF (20 mL) and stirred at 25° C. for 16 hours. Sulfuric acid (1.0M, 50 mL) was added, extracted with diethyl ether (2×60 mL) and the organic solvent dried using magnesium sulfate and evaporated. The residue was distilled at 0.25 mmHg to obtain 3.06 g (51% yield, b.p. 98°-100° C.)13-tetradecenyl chloride as a colourless liquid.

Workup

  1. additionafter the addition
  2. stirringstirred at 25° C. for 16 hours
  3. extractionextracted with diethyl ether (2×60 mL)
  4. customthe organic solvent dried
  5. customevaporated
  6. distillationThe residue was distilled at 0.25 mmHg

Sources & evidence

ORD record
ord-d169f8e9ea22426cac33433081583b67
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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