Triethylamine → 4-Methanesulfonyl-6-methyl-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 1295557Notes

Reaction equation

HRID 1295557 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][NH:7][C:6]=2[CH:11]=1.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[CH3:19][S:20]([N:7]1[C:6]2[CH:11]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=2[O:10][CH2:9][CH2:8]1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 6494096-methyl-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 694178614-Methanesulfonyl-6-methyl-3,4-dihydro-2H-benzo[1,4]oxazineYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine (1.49 g, 10 mmol) was dissolved in dichloromethane (50 mL) and treated with triethylamine (1.14 g, 11 mmol) followed by the dropwise addition of methanesulfonyl chloride (1.26 g, 11 mmol). The mixture was stirred at ambient temperature for 18 h then evaporated to dryness under reduced pressure. The residue was partitioned between ethyl acetate and saturated aqueous NaHCO3. The phases were separated and the organic phase washed with water, saturated brine, dried (MgSO4) and evaporated to dryness under reduced pressure to give the title compound (2.09 g, 93%) as a brown solid.

Workup

  1. customthen evaporated to dryness under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and saturated aqueous NaHCO3
  3. customThe phases were separated
  4. washthe organic phase washed with water, saturated brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-028e2a324f354eb7aea644437ba0f178
Source dataset
uspto-grants-2007_07
Patent number
US07244726B2

Reaction notes

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