Pyridine → 4-[2-(2,3-Dihydro-benzo[1,4]oxazin-4-yl)-ethoxy]benzaldehyde

HRID 848965Notes

Reaction equation

CS([O:5][CH2:6][CH2:7][N:8]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[O:11][CH2:10][CH2:9]1)(=O)=O.[O:18]1C2C=CC=CC=2N(CCO)C[CH2:19]1.[CH3:31]S(Cl)(=O)=O.N1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[O:11]1[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:8]([CH2:7][CH2:6][O:5][C:37]2[CH:31]=[CH:41][C:40]([CH:19]=[O:18])=[CH:39][CH:38]=2)[CH2:9][CH2:10]1

Participants

Reactant 4

HCID 1049Pyridine

HCID 31297Methanesulfonyl chloride

HCID 104225902-(2,3-Dihydro-1,4-benzoxazin-4-yl)ethyl methanesulfonate

HCID 176087282-(2,3-Dihydro-4H-1,4-benzoxazin-4-YL)ethanol

Product 1

HCID 109897044-[2-(2,3-Dihydro-benzo[1,4]oxazin-4-yl)-ethoxy]benzaldehydeYield 61%

Conditions

Temperature: 25 °C

Procedure

Preparation of 2-(2,3-dihydro-1,4-benzoxazine-4-yl)ethyl methanesulfonate--To a solution of 2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethanol (17.0 g, 94.9 mmol) in pyridine (200 ml) was added methanesulfonyl chloride (16.31 g, 142.0 mmol) dropwise at 0° C. The reaction mixture was stirred for 10 h at 25° C. Ice water (200 ml) was added and the mixture was extracted with ethyl acetate (2×100 ml). The combined organic extracts were washed with 2N HCl (3×75 ml), water (75 ml), brine (50 ml) and dried (Na2SO4). The solvent was evaporated under reduced pressure. The residue was triturated with 5% ethyl acetate in pet. ether to afford the title compound (15.0 g, 61%) as brown solid. mp. 92-95° C.

Workup

extractionthe mixture was extracted with ethyl acetate (2×100 ml)
washThe combined organic extracts were washed with 2N HCl (3×75 ml), water (75 ml), brine (50 ml)
dry with materialdried (Na2SO4)
customThe solvent was evaporated under reduced pressure
customThe residue was triturated with 5% ethyl acetate in pet. ether

Sources & evidence

ORD record: ord-65ac4a8858254120af0db1f3c5473ad5
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06011031

Reaction notes

Loading…