Ethyl Acetate → (+/-)-5-chloro-4-(3,4-difluorobenzyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one

HRID 2117281Notes

Reaction equation

HRID 2117281 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]([OH:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=1.[C:20](OCC)(=[O:22])C>>[Cl:8][C:4]1[C:3]2[CH:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=3)[O:19][C:20](=[O:22])[NH:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 69318113(+/-)-1-(2-Amino-6-chlorophenyl)-2-(3,4-difluorophenyl)ethanol

Product 1

HCID 69315430(+/-)-5-chloro-4-(3,4-difluorobenzyl)-1,4-dihydro-2H-3,1-benzoxazin-2-oneYield 64%

Procedure

This compound was prepared using General Method 2 (EXAMPLE 1) from (±)-1-(2-amino-6-chlorophenyl)-2-(3,4-difluorophenyl)ethanol (0.28 g, 1.1 mmol) to afford 0.21 g (64%) of (±)-5-chloro-4-(3,4-difluorobenzyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one after flash chromatography (4:1 hexanes:ethyl acetate).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-880ff0ba66ce4620b60c7bee49fd0f89
Source dataset
uspto-grants-2008_10
Patent number
US07442696B2

Reaction notes

Loading…