Ethanol → 6-(2-morpholinoacetyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 1184435Notes

Reaction equation

HRID 1184435 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]2[O:9][CH2:10][C:11](=[O:13])[NH:12][C:7]=2[CH:6]=1)=[O:4].CCO.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CCOCC>[O:22]1[CH2:23][CH2:24][N:19]([CH2:2][C:3]([C:5]2[CH:15]=[CH:14][C:8]3[O:9][CH2:10][C:11](=[O:13])[NH:12][C:7]=3[CH:6]=2)=[O:4])[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 702EthanolHCID 8083MorpholineHCID 27644586-(2-chloroacetyl)-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 1

HCID 450345006-(2-morpholinoacetyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

To a 20 mL scintillation vial with a magnetic stirrer was added commercially available 6-(2-chloroacetyl)-2H-benzo[b][1,4]oxazin-3(4H)-one (113 mg, 0.5 mmol) and EtOH (2.5 mL) followed by morpholine (96 mg, 1.1 mmol). The reaction was heated at 80° C. for 1 h then cooled to room temperature. The solution was diluted with Et2O (10 mL) and the resulting solid was isolated by filtration, washed with Et2O and dried in vacuo to give a white solid: 1H NMR (DMSO-d6, 400 MHz): δ=10.91 (s, 1H), 9.31 (br. s., 1H), 7.65 (dd, J=8.3, 2.0 Hz, 1H), 7.55 (d, J=2.0 Hz, 1H), 7.03 (d, J=8.3 Hz, 1H), 4.68 (s, 2H), 3.67-3.87 (m, 6H), 3.58 (t, J=4.3 Hz, 2H), 3.07 ppm (d, J=5.1 Hz, 2H). ESI-MS: m/z 277.1 (M+H)+.

Workup

  1. temperaturethen cooled to room temperature
  2. customthe resulting solid was isolated by filtration
  3. washwashed with Et2O
  4. customdried in vacuo
  5. customto give a white solid

Sources & evidence

ORD record
ord-a0a5efa77061409390d9c7c2f81a7647
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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