Methanesulfonyl chloride → HCID 19087664, compound

HRID 1464280Notes

Reaction equation

HRID 1464280 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[NH:8][C:7]1=[O:17].[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(N(CC)CC)C>[CH3:18][S:19]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[NH:8][C:7]1=[O:17])(=[O:21])=[O:20]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 19087700HCID 19087700, compound

Product 1

HCID 19087664HCID 19087664, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred suspension of 1-[4-hydroxybutyl)-2,4(1H,3H)-quinazolinedione (778 mg) in chloroformtetrahydrofuran (40 ml, 1:1 V/V) was added methanesulfonyl chloride (0.57 ml), and triethylamine (1.85 ml) on an ice-bath. After stirring for 18 hours at room temperature, the reaction mixture was heated at 50° C. for 30 hours with stirring. After evaporation of the solvents the residue was diluted with ethyl acetate. The mixture was washed in turn with water and brine, dried over magnesium sulfate, and evaporated. 1-(4-Methanesulfonyloxybutyl)-2,4(1H,3H)-quinazolinedione (675 mg) as a crystal was obtained by recrystallization from methanol.

Workup

  1. temperaturethe reaction mixture was heated at 50° C. for 30 hours
  2. stirringwith stirring
  3. customAfter evaporation of the solvents the residue
  4. additionwas diluted with ethyl acetate
  5. washThe mixture was washed in turn with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-7b3d357ce3274d7a8afe3e3946d09bcf
Source dataset
uspto-grants-1994_04
Patent number
US05304560

Reaction notes

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