Water → HCID 22593940, compound

HRID 848968Notes

Reaction equation

HRID 848968 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][CH2:3][CH2:2]1.Br[CH2:12][C:13]1[O:14][C:15]2[CH:21]=[CH:20][C:19]([CH:22]=[O:23])=[CH:18][C:16]=2[CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].CN(C)C=O>[CH:22]([C:19]1[CH:20]=[CH:21][C:15]2[O:14][C:13]([CH2:12][N:4]3[C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[O:1][CH2:2][CH2:3]3)=[CH:17][C:16]=2[CH:18]=1)=[O:23]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5850963,4-Dihydro-2H-1,4-benzoxazineHCID 22118749HCID 22118749, compound

Product 1

HCID 22593940HCID 22593940, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2,3-dihydro-1,4-benzoxazine (1.07 g, 7.94 mmol), 2-bromomethyl-5-formyl benzofuran (1.9 g, 7.94 mmol), potassium carbonate (5.5 g, 39.74 mmol) and Aliquat 336 (2 drops) in dimethyl formamide (25 ml) was stirred at 65° C. for 8 h. Water (50 ml) was added to reaction mixture and extracted with ethyl acetate (2×50 ml). The extracts were washed with water (50 ml), brine (50 ml) and dried (Na2SO4). The solvent was evaporated to dryness and the residue was chromatographed over silica gel using a mixture of ethyl acetate pet. ether (3:7) as an eluent to afford the title compound (2.1 g, 91%) as an oil.

Workup

  1. extractionextracted with ethyl acetate (2×50 ml)
  2. washThe extracts were washed with water (50 ml), brine (50 ml)
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was evaporated to dryness
  5. customthe residue was chromatographed over silica gel using
  6. additiona mixture of ethyl acetate pet. ether (3:7) as an eluent

Sources & evidence

ORD record
ord-a7822dc683e840339926b0bbf57c7fd6
Source dataset
uspto-grants-2000_01
Patent number
US06011031

Reaction notes

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