Dimethylformamide → 5-Methoxy-2-nitrobenzamide

HRID 1406979Notes

Reaction equation

HRID 1406979 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH:11]=1)[C:8](O)=[O:9].S(Cl)(Cl)=O.C[N:20](C=O)C>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH:11]=1)[C:8]([NH2:20])=[O:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 3392095-Methoxy-2-nitrobenzoic acid

Product 1

HCID 184039495-Methoxy-2-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of 5-methoxy-2-nitrobenzoic acid (7.5 g, 38.0 mmol) in anhydrous benzene (50 mL), was added thionyl chloride (3.8 mL, 52.05 mmol) followed by the addition of anhydrous DMF (0.4 mL). The resulting reaction mixture was refluxed for 5 h, upon which the volatiles were removed in vacuo. The residue was dissolved in anhydrous THF (60 mL) and added to an ice-cold saturated solution of ammonia in THF (60 mL). The resulting heterogeneous reaction mixture was allowed to warm room temperature and stirring was continued at RT for 48 h. The s volatiles were removed in vacuo and the residue was used without further purification for next step. HPLC retention time 3.29 mins.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 5 h, upon which the volatiles
  3. customwere removed in vacuo
  4. dissolutionThe residue was dissolved in anhydrous THF (60 mL)
  5. additionadded to an ice-cold saturated solution of ammonia in THF (60 mL)
  6. customThe s volatiles were removed in vacuo
  7. customthe residue was used without further purification for next step

Sources & evidence

ORD record
ord-4c4dd57674c047b08d07f3724a596841
Source dataset
uspto-grants-2014_12
Patent number
US08916576B2

Reaction notes

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