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

HRID 340658
Notes
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Reaction equation

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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 69462-NitroanilineHCID 24386Thionyl ChlorideHCID 2263354-(Benzyloxy)-3-methoxybenzoic acid

Product 1

HCID 66911323N-(2-nitrophenyl)-4-benzyloxy-3-methoxybenzamideYield 51.5%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 1049PyridineSolvent
HCID 6344DichloromethaneSolvent

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

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

Sources & evidence

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

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes