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

HRID 2117278Notes

Reaction equation

HRID 2117278 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[OH:10].[C:18](OCC)(=[O:20])C>>[Cl:8][C:4]1[C:3]2[CH:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[O:10][C:18](=[O:20])[NH:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 69315535(+/-)-(2-Amino-6-chlorophenyl)-(4-fluorophenyl)methanol

Product 1

HCID 69317854(+/-)-5-chloro-4-(4-fluorophenyl)-1,4-dihydro-2H-3,1-benzoxazin-2-oneYield 45%

Procedure

This compound was prepared using General Method 2 (EXAMPLE 1) from (±)-1-(2-amino-6-chlorophenyl)-(4-fluorophenyl)methanol (0.28 g, 1.1 mmol) to afford 0.14 g (45%) of (±)-5-chloro-4-(4-fluorophenyl)-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-dd2961dc935d4cfc9f927a65e25b5586
Source dataset
uspto-grants-2008_10
Patent number
US07442696B2

Reaction notes

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