4-Nitrobenzoyl chloride → N-(1,3-benzodioxol-5-yl)-4-nitrobenzamide

Reaction equation

[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=2[O:2]1.[N+:11]([C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1)([O-:13])=[O:12]>>[N+:11]([C:14]1[CH:15]=[CH:16][C:17]([C:18]([NH:6][C:5]2[CH:7]=[CH:8][C:9]3[O:10][CH2:1][O:2][C:3]=3[CH:4]=2)=[O:19])=[CH:21][CH:22]=1)([O-:13])=[O:12]

Participants

Reactant 2

HCID 85024-Nitrobenzoyl chloride

HCID 843101,3-Benzodioxol-5-amine

Product 1

HCID 674221N-(1,3-benzodioxol-5-yl)-4-nitrobenzamideYield 87.2%

Procedure

Using 3,4-methylenedioxyaniline (1.44 g, 10.5 mmol) and 4-nitrobenzoyl chloride (1.86 g, 10.0 mmol), the procedure of Reference Example 11 was repeated to obtain 2.49 g (87.2%) of the title compound in the form of yellow crystals.

Sources & evidence

ORD record: ord-b04fe9c2f1da4526a30f3f2067ac49b1
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05728835

Reaction notes

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