Chloroacetyl chloride → 6-Phenyl-4H-benzo[1,4]oxazin-3-one

HRID 417918Notes

Reaction equation

HRID 417918 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][C:3]=1[OH:14].C(N(CC)CC)C.Cl[CH2:23][C:24](Cl)=[O:25].[H-].[Na+]>C1COCC1>[C:8]1([C:6]2[CH:5]=[CH:4][C:3]3[O:14][CH2:23][C:24](=[O:25])[NH:1][C:2]=3[CH:7]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 145622-Amino-4-phenylphenolHCID 24758Sodium hydride

Product 1

HCID 115794776-Phenyl-4H-benzo[1,4]oxazin-3-oneYield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using 2-amino-4-phenylphenol (1 g, 5.4 mmol), triethylamine (0.97 mL, 7.0 mmol) and chloroacetyl chloride (0.72 g, 5.9 mmol) in THF (35 mL) followed by sodium hydride (0.27 g of a 60% suspension in oil, 6 mmol) to yield the title compound as a pale yellow solid (1.2 g, 91%). δH (DMSO-d6) 4.62 (2H, s), 7.29-7.56 (8H, m), 10.81 (1H, s).

Sources & evidence

ORD record
ord-545c08162c054aa1a818abe0a1fbf826
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

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