Dimethylformamide → 2-Methyl-4-nitrobenzamide

HRID 509237노트

반응식

HRID 509237 반응식
[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C[N:15](C=O)C.C(Cl)(=O)C(Cl)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:15])=[O:5]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 747904-Nitro-o-toluic acid

생성물 1

HCID 201651202-Methyl-4-nitrobenzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 2-methyl-4-nitrobenzoic acid suspended in CH2Cl2 under Ar was added DMF then oxalyl chloride. The reaction was stirred at room temperature 1.5 hours then the solvent was evaporated. The residue was dissolved in THF and ammonia gas was bubbled through the reaction for 15 minutes. The solvent was evaporated and the residue partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The extracts were dried (MgSO4), filtered and evaporated. Column chromatography (SiO2, 0-100% EtOAc/Hex) gave pure 2-methyl-4-nitrobenzamide (E111).

후처리

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in THF
  3. customammonia gas was bubbled through the reaction for 15 minutes
  4. customThe solvent was evaporated
  5. customthe residue partitioned between EtOAc and water
  6. extractionThe aqueous layer was extracted with EtOAc
  7. dry with materialThe extracts were dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

출처 및 근거

ORD 기록
ord-7b51697cfdbc4cee9b97884fae5f6df4
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096569B2

반응 노트

불러오는 중…