Dimethylformamide → 5-Methoxy-2-nitrobenzamide

HRID 1808491Notes

Reaction equation

HRID 1808491 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-65275d30382a4b44aac270a03a0125c2
Source dataset
uspto-grants-2013_01
Patent number
US08357693B2

Reaction notes

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