Water → 2-(Phenoxazin-10-yl)ethyl methanesulfonate

HRID 2219780Notes

Reaction equation

HRID 2219780 reaction equation
[CH:1]1[C:14]2[N:13]([CH2:15][CH2:16][OH:17])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27].O>ClCCl>[CH3:25][S:26]([O:17][CH2:16][CH2:15][N:13]1[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[O:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:28])=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1017692410H-Phenoxazine-10-ethanol

Product 1

HCID 112204632-(Phenoxazin-10-yl)ethyl methanesulfonateYield 235.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(10H-phenoxazin-10-yl)-1-ethanol (4.6 g, 20.28 mmol) in dichloromethane (20 ml) was added triethylamine (1.06 g, 10.56 mmol) under an atmosphere of nitrogen at 25° C. Methanesulfonyl chloride (0.90 g, 7.92 mmol) was added to the above reaction mixture at 0° C. and stirring was continued for further 3 h at 25° C. Water (50 ml) was added, and aqueous phase extracted with chloroform (2×25 ml). The combined organic phases were washed with water (25 ml), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was triturated with petroleum ether to afford the title compound (5.7 g, 92%) as a solid. mp: 81-83° C.

Workup

  1. extractionaqueous phase extracted with chloroform (2×25 ml)
  2. washThe combined organic phases were washed with water (25 ml)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was triturated with petroleum ether

Sources & evidence

ORD record
ord-553566e04d314befb9e230da4ba3a8b3
Source dataset
uspto-grants-2008_08
Patent number
US07414128B2

Reaction notes

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