Water → 7-fluoro-6-(2-nitrobenzoyl)amino-2H-1,4-benzoxazin-3-(4H)-one

HRID 380286Notes

Reaction equation

HRID 380286 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].[F:13][C:14]1[C:24]([NH2:25])=[CH:23][C:17]2[NH:18][C:19](=[O:22])[CH2:20][O:21][C:16]=2[CH:15]=1.C(N(CC)CC)C.O>C(Cl)Cl>[F:13][C:14]1[C:24]([NH:25][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[N+:1]([O-:3])=[O:2])=[CH:23][C:17]2[NH:18][C:19](=[O:22])[CH2:20][O:21][C:16]=2[CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 118752-Nitrobenzoyl chlorideHCID 103133897-Fluoro-6-amino-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 183646287-fluoro-6-(2-nitrobenzoyl)amino-2H-1,4-benzoxazin-3-(4H)-oneYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-nitro-benzoyl chloride (2.04 g, 90% purity, 10 mmol) in CH2Cl2 (20 mL) was added dropwise into a mixture of 7-fluoro-6-amino-2H-1,4-benzoxazin-3-(4H)-one (1.78 g, 10 mmol) and triethylamine (1.1 g, 11 mmol) in CH2Cl2 (20 mL) over 10 min with ice-water bath cooling. The reaction mixture was then stirred at room temperature overnight. The mixture was poured into water and the resulting precipitate was collected by suction-filtration and washed with hexane and then water to give 7-fluoro-6-(2-nitrobenzoyl)amino-2H-1,4-benzoxazin-3-(4H)-one, 2.9 g (yield: 92%) as a solid: mp >248° C.

Workup

  1. temperaturecooling
  2. filtrationthe resulting precipitate was collected by suction-filtration
  3. washwashed with hexane

Sources & evidence

ORD record
ord-7b4227860f1d48df9f9a3d9a9e65d3eb
Source dataset
uspto-grants-2001_10
Patent number
US06303542B1

Reaction notes

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