Dimethylformamide → N-(2-nitrophenyl)-4-benzyloxy-3-methoxybenzamide

HRID 340658

Reaction equation

[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.S(Cl)(Cl)=O.[N+:29]([C:32]1[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=1[NH2:34])([O-:31])=[O:30]>C(Cl)Cl.O.N1C=CC=CC=1>[N+:29]([C:32]1[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=1[NH:34][C:13](=[O:15])[C:12]1[CH:16]=[CH:17][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:10]([O:18][CH3:19])[CH:11]=1)([O-:31])=[O:30]

Participants

Conditions

Temperature: 50 °C

Procedure

In 20 ml of methylene chloride was suspended 2.0 g (7.7 mmol) of 4-benzyloxy-3-methoxy benzoic acid. DMF (0.05 g) and thionyl chloride (0.68 ml) were added to this suspension. The mixture was stirred at 50° C. for 2 hours. At a temperature of 0° C., 20 ml of pyridine wherein 1.1 g (8.0 mmol) of 2-nitroaniline had been dissolved at room temperature was added dropwise to the mixture. The mixture was stirred for 2 hours at room temperature, and water was added thereto to extract the methylene chloride phase. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The crystals thus obtained were recrystallized using methylene chloride-hexane, thereby yielding 1.5 g of N-(2-nitrophenyl)-4-benzyloxy-3-methoxybenzamide crystals.

Workup

additionwas added dropwise to the mixture
stirringThe mixture was stirred for 2 hours at room temperature
extractionto extract the methylene chloride phase
dry with materialThe extract was dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off
customThe crystals thus obtained
customwere recrystallized

Sources & evidence

ORD record: ord-e98c02bf78c5443a92616f03a336d994
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895599B2

Linked notes

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