Oxalyl chloride → 2-(4-Tert-butylphenyl)-6-nitro-3,1-benzoxazin-4-one

HRID 395715

Reaction equation

HRID 395715 reaction equation
[C:1]([C:5]1[CH:25]=[CH:24][C:8]([C:9]([NH:11][C:12]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:13]=2[C:14]([OH:16])=[O:15])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O>C(Cl)Cl.CN(C)C=O>[N+:21]([C:18]1[CH:19]=[CH:20][C:12]2[N:11]=[C:9]([C:8]3[CH:24]=[CH:25][C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])=[CH:6][CH:7]=3)[O:16][C:14](=[O:15])[C:13]=2[CH:17]=1)([O-:23])=[O:22]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 104974752-(4-Tert-butylbenzoylamino)-5-nitrobenzoic acid

Product 1

HCID 3855992-(4-Tert-butylphenyl)-6-nitro-3,1-benzoxazin-4-oneYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-(4-tert-butylbenzoylamino)-5-nitrobenzoic acid (37.1 g, 108 mmol) and N,N-dimethylformamide (0.4 mL, 5.4 mmol) in methylene chloride (200 mL) was added oxalyl chloride (10.4 mL, 119 mmol) in a dropwise manner. After stirring for 2 h, the mixture was filtered and the small amount of black solid was discarded. The filtrate was concentrated in vacuo to give 32.9 g (94%) of the title compound as a light brown solid; mp 159-61° C.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-159aa5ac036241c6bc2e4953074162ae
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Linked notes

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