Trimethylamine → HCID 86749996, compound

HRID 1900820Notes

Reaction equation

HRID 1900820 reaction equation
[CH2:1]([OH:6])/[CH:2]=[CH:3]\[CH2:4][CH3:5].CN(C)C.[CH3:11][S:12](Cl)(=[O:14])=[O:13]>CCOCC>[S:12]([O:6][CH2:1]/[CH:2]=[CH:3]\[CH2:4][CH3:5])([CH3:11])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 31297Methanesulfonyl chlorideHCID 5364919cis-Pent-2-ene-1-ol

Product 1

HCID 86749996HCID 86749996, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Z-2-Penten-1-ol (5.0 g, 58.1 mmol), trimethylamine (6.45 g, 63.9 mmol), methanesulfonylchloride (7.0 g, 61.1 mmol) and ether (30 ml) were allowed to react at ambient temperature for 1 hour. After the completion of the reaction, the insoluble matter was removed and washed with water. The washed substance was dried over sodium sulfate. The solvent was distilled off to obtain 7.95 g of Z-1-mesyloxy-2-pentene as pale yellow oily material (83.4%). This material was added to a mixture of 3,8-dimethyl-5-hydroxycarbostyril (7.0 g, 37.0 mmol), potassium carbonate (10.2 g, 74.0 mmol) and dimethylformamide (210 ml), and allowed to react at 70° C. for 1 hour. The reaction mixture was condensed under reduced pressure, and the residue was poured into water to obtain 7.36 g of the title compound as a brown solid (77.3%).

Workup

  1. customto react at ambient temperature for 1 hour
  2. customAfter the completion of the reaction
  3. customthe insoluble matter was removed
  4. washwashed with water
  5. dry with materialThe washed substance was dried over sodium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-9333727f4f52455d9e0b365f6597994b
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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