Water → 3-(4-Ethyl-2,2,7-trimethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4-hydroxy-benzaldehyde

HRID 2239244Notes

Reaction equation

[CH2:1]([N:3]1[C:8]2[CH:9]=[C:10]([C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=3[O:22]C)[CH:17]=[O:18])[C:11]([CH3:13])=[CH:12][C:7]=2[O:6][C:5]([CH3:25])([CH3:24])[C:4]1=[O:26])[CH3:2].[S-]CC.[Na+].O>CN(C=O)C>[CH2:1]([N:3]1[C:8]2[CH:9]=[C:10]([C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=3[OH:22])[CH:17]=[O:18])[C:11]([CH3:13])=[CH:12][C:7]=2[O:6][C:5]([CH3:25])([CH3:24])[C:4]1=[O:26])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of Compound 2A (240 mg, 0.68 mmol) in 3 mL of dry DMF was treated with sodium thioethoxide (143 mg, 1.7 mmol). The reaction flask was then equipped with a reflux condenser, nitrogen inlet and heated to 80° C. for 2 hours. The reaction mixture was allowed to cool to room temperature and 5 mL of water is added and the reaction mixture passed through a SPE. The crude compound was eluted with EtOAc. The collected eluant was dried of excess solvent to yield product which was used without further purification in the next step. MS (electrospray): mass calculated for C20H21NO4, 339.15 m/z found 340.1, [M+H]+.

Workup

customThe reaction flask was then equipped with a reflux condenser, nitrogen inlet
temperatureto cool to room temperature
washThe crude compound was eluted with EtOAc
customThe collected eluant was dried of excess solvent
customto yield product which
customwas used without further purification in the next step

Sources & evidence

ORD record: ord-6d94434258a54574a84e160fafcb176f
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723326B2

Reaction notes

Loading…