Chloroacetyl chloride → 6-Methoxy-3,4-dihydro-2H-1,4-benzoxazine

HRID 1167610Notes

Reaction equation

HRID 1167610 reaction equation
[NH2:1][C:2]1(O)C=CC(OC)=C[CH2:3]1.[C:11](=O)([O-])O.[Na+].Cl[CH2:17][C:18](Cl)=[O:19].[CH2:21]([C:25]([CH3:27])=[O:26])[CH:22](C)C>>[CH3:11][O:19][C:18]1[CH:22]=[CH:21][C:25]2[O:26][CH2:3][CH2:2][NH:1][C:27]=2[CH:17]=1

Participants

5

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 7909Methyl Isobutyl KetoneHCID 516892Sodium BicarbonateHCID 22993362HCID 22993362, compound

Product 1

HCID 162444606-Methoxy-3,4-dihydro-2H-1,4-benzoxazine

Procedure

The compound obtained in Step A (5.94 g; 42.7 mmol) is dissolved in 50 ml of methyl isobutyl ketone, and a solution of sodium hydrogen carbonate (3 eq.; 128.1 mmol; 10.76 g dissolved in 60 ml of water) is subsequently added. Chloroacetyl chloride (1.1 eq.; 46.9 mmol; 3.74 ml) is then slowly added. The mixture is maintained at reflux for one hour, then the methyl isobutyl ketone is removed under reduced pressure. The residue is taken up in ethyl acetate, and the organic phase is washed twice with water, dried over MgSO4, and subsequently removed under reduced pressure to yield the title product in the form of a solid.

Workup

  1. temperatureThe mixture is maintained
  2. temperatureat reflux for one hour
  3. customthe methyl isobutyl ketone is removed under reduced pressure
  4. washthe organic phase is washed twice with water
  5. dry with materialdried over MgSO4
  6. customsubsequently removed under reduced pressure

Sources & evidence

ORD record
ord-c6432d1421b849cc93cbfc4aa75d3978
Source dataset
uspto-grants-2003_09
Patent number
US06620809B2

Reaction notes

Loading…