5-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione → 6-amino-3-bromo-2-chloro-N-methylbenzamide

HRID 2279787Notes

Reaction equation

HRID 2279787 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH:10][CH3:11])=[O:9])=[C:6](F)[C:5]([Br:13])=[CH:4][CH:3]=1.FC1C2C(=O)OC(=O)NC=2C=CC=1.[Cl:27]C1C2C(=O)OC(=O)NC=2C=CC=1>>[NH2:1][C:2]1[C:7]([C:8]([NH:10][CH3:11])=[O:9])=[C:6]([Cl:27])[C:5]([Br:13])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6390585-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione2×HCID 27830576-Fluoroisatoic anhydrideHCID 866977326-amino-3-bromo-2-fluoro-N-methylbenzamide

Product 1

HCID 866977366-amino-3-bromo-2-chloro-N-methylbenzamide

Procedure

Prepared analogously to Compound 27D replacing 5-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (Compound 27E) with 5-Chloro-1H-benzo[d][1,3]oxazine-2,4-dione (Compound 28E). 1H NMR (CDCl3, 500 MHz) δ=2.95 (d, J=5.2 Hz, 3H), 6.02 (brs, 2H), 6.89 (d, J=8.8 Hz, 1H), 7.25 (d, J=8.8 Hz, 1H), 7.79 (brs, 1H).

Sources & evidence

ORD record
ord-3d59b41ad3094b139e8589a573d6f5ed
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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