Triethylamine → 5-(2-(Methanesulfonyloxy)ethoxy)-2-methylquinazoline

HRID 1349949Notes

Reaction equation

HRID 1349949 reaction equation
[CH3:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH2:13][CH2:14][OH:15])[N:3]=1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[CH3:23][S:24]([O:15][CH2:14][CH2:13][O:12][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[N:11][C:2]([CH3:1])=[N:3]2)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 17965146HCID 17965146, compound

Product 1

HCID 179651395-(2-(Methanesulfonyloxy)ethoxy)-2-methylquinazolineYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(2-methylquinazolin-5-yloxy)ethanol (0.330 g, 1.62 mmol) in dichloromethane (20 mL) and triethylamine (0.34 mL, 2.43 mmol) was added methane sulfonyl chloride (0.14 mL, 1.78 mmol) dropwise. The reaction mixture was allowed to stir at room temperature for 2 h. The reaction mixture was diluted with further dichloromethane and partitioned with saturated NaHCO3 aq. The organic phase was washed with brine, dried (MgSO4) and evaporated in vacuo to give the title compound as a cream solid (0.452 g, 99%).

Workup

  1. custompartitioned with saturated NaHCO3 aq. The organic phase
  2. washwas washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-67a60fbbd19a4a8faa04c4f341ee8969
Source dataset
uspto-grants-2007_05
Patent number
US07214674B2

Reaction notes

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