Chloroacetyl chloride → 6-Chloro-7-nitro-2H-1,4-benzoxazin-3(4H)-one

HRID 417920Notes

Reaction equation

HRID 417920 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].C(N(CC)CC)C.Cl[CH2:21][C:22](Cl)=[O:23].[H-].[Na+]>C1COCC1>[Cl:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]2[O:12][CH2:21][C:22](=[O:23])[NH:1][C:2]=2[CH:7]=1

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 24758Sodium hydrideHCID 38948482-Amino-4-chloro-5-nitrophenol

Product 1

HCID 33056966-Chloro-7-nitro-2H-1,4-benzoxazin-3(4H)-oneYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using 2-amino-4-chloro-5-nitrophenol (3.0 g, 15 mmol), triethylamine (2.7 mL, mmol) and chloroacetyl chloride (2.0 g, 17 mmol) in THF (100 mL) followed by sodium hydride (1.3 g of a 60% suspension in oil, 30 mmol) to yield the title compound as an orange solid (1.8 g, 54%). δH (DMSO-d6) 4.74 (2H, s), 7.07 (1H, s), 7.77 (1H, s), 11.29 (1H, br s).

Sources & evidence

ORD record
ord-c5ec4ee185f24d4e9b62194dbea63704
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

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