Water → HCID 21893842, compound

HRID 393549Notes

Reaction equation

HRID 393549 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH:4]([CH2:12][OH:13])[CH2:3]1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].O>ClCCl>[CH3:21][S:22]([O:13][CH2:12][CH:4]1[CH2:3][N:2]([CH3:1])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5]1)(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10797435HCID 10797435, compound

Product 1

HCID 21893842HCID 21893842, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-methanol (6.0 g, 33.51 mmol) in dichloromethane (20 mL) was added triethylamine (10.15 g, 100.5 mmol) under nitrogen atmosphere at 25° C. Methanesulfonyl chloride (5.75 g, 50.25 mmol) was added to the above reaction mixture at 0° C. and stirring was continued for further 10 h at 25° C. Water (50 mL) was added and extracted with chloroform (2×25 mL). The combined organic extracts were washed with water (50 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was chromatographed over silica gel using a mixture of ethyl acetate and hexane (2:8) to yield (4-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methyl methanesulfonate (3.7 g, 43%) as a syrup.

Workup

  1. extractionextracted with chloroform (2×25 mL)
  2. washThe combined organic extracts were washed with water (50 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was chromatographed over silica gel using
  7. additiona mixture of ethyl acetate and hexane (2:8)

Sources & evidence

ORD record
ord-2f88cc49fb7a4c87ad4bde16ca69a64c
Source dataset
uspto-grants-2004_10
Patent number
US06809095B2

Reaction notes

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