Dimethylformamide → Methyl 3-carbamoyl-5-nitrobenzoate

HRID 964488

반응식

HRID 964488 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([O-:16])=O)[CH:7]=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])([O-:3])=[O:2].S(Cl)(Cl)=O.C[N:22](C=O)C>C1COCC1.C(Cl)Cl>[CH3:12][O:11][C:9]([C:8]1[CH:7]=[C:6]([CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=1)[C:14]([NH2:22])=[O:16])=[O:10]

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 6931682Monomethyl-5-nitroisophthalate

생성물 1

HCID 3741295Methyl 3-carbamoyl-5-nitrobenzoate수율 81%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of mono-methyl 5-nitroisophthalate (45.0 g, 200 mmol), thionyl chloride (71.4 g, 600 mmol) and DMF through SiO2 (125 μL) in dry THF (100 mL) and dry CH2Cl2 (300 mL) was refluxed overnight. The reaction mixture was evaporated in vacuo and then added dry CH2Cl2 (200 mL) and hexanes (500 mL). Ammonia gas was introduced into the solution and the precipitation was collected on a glass-filter. The cake was suspended in 1N HCl (500 mL), filtered again and then washed with saturated NaHCO3 aq. (500 mL) and water (500 mL). The product was dried in vacuo to give ivory powder (36.3 g, 81%): 1H NMR (300 MHz, DMSO-d6) δ 8.918 (t, J=1.8 Hz, 1H), 8.816 (t, J=1.2 Hz, 1H), 8.773 (t, J=1.6 Hz, 1H), 8.716 (s, 1H, NH), 7.859 (s, 1H, NH), 3.944 (s, 3H); 13C NMR (300 MHz, DMSO-d6) δ 164.9, 164.2, 148.1, 136.4, 134.9, 133.8, 133.3, 131.5, 126.4, 126.0, 53.1.

후처리

  1. customThe reaction mixture was evaporated in vacuo
  2. additionadded dry CH2Cl2 (200 mL) and hexanes (500 mL)
  3. additionAmmonia gas was introduced into the solution
  4. customthe precipitation
  5. customwas collected on a glass-filter
  6. filtrationfiltered again
  7. washwashed with saturated NaHCO3 aq. (500 mL) and water (500 mL)
  8. customThe product was dried in vacuo

출처 및 근거

ORD 기록
ord-9185880f43a44e2e82eabc2400ba6969
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05770380

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