Ethyl 2-aminobenzoate → Ethyl 2-[3-(2-furyl)acrylamido]benzoate

HRID 1084822노트

반응식

HRID 1084822 반응식
[I-].ClC1C=CC=C[N+]=1C.[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]=[CH:16][C:17]([OH:19])=O.C(N(CC)CC)C.[NH2:27][C:28]1[CH:38]=[CH:37][CH:36]=[CH:35][C:29]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31]>C(Cl)Cl>[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]=[CH:16][C:17]([NH:27][C:28]1[CH:38]=[CH:37][CH:36]=[CH:35][C:29]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:19]

참가 물질

6

반응물 4

HCID 6877Ethyl 2-aminobenzoateHCID 8471TriethylamineHCID 10876Furylacrylic acidHCID 1670692-Chloro-1-methylpyridinium iodide

생성물 1

HCID 4450927Ethyl 2-[3-(2-furyl)acrylamido]benzoate수율 30.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

Under nitrogen stream, 2-chloro-1-methylpyridinium iodide (1.272 g, 4.34 mmol) was suspended in dry methylene chloride (5 ml). To the suspension a solution of 3-(2-furyl)acrylic acid (500 mg, 3.62 mmol), triethylamine (1.2 ml, 8.69 mmol), and ethyl 2-aminobenzoate (0.53 ml, 3.62 mmol) in dry methylene chloride (5 ml) was added. The mixture was heated under reflux for 40 hours. Then, the reaction mixture was diluted with methylene chloride, and washed with 10% aqueous HCl, saturated aqueous sodium chloride, 1N-aqueous NaOH, and saturated aqueous sodium chloride successively, and dried. Removal of solvent gave a viscous oil, which, on washing with n-hexane gave white solids of the title compound (312 mg, yield: 30.2%), which was recrystallized from methanol. m.p., 85°-86° C.

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 40 hours
  3. washwashed with 10% aqueous HCl, saturated aqueous sodium chloride, 1N-aqueous NaOH, and saturated aqueous sodium chloride successively
  4. customdried
  5. customRemoval of solvent
  6. customgave a viscous oil, which
  7. washon washing with n-hexane

출처 및 근거

ORD 기록
ord-9cb8dfb2cb994905a60b3a6f3c499400
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05006548

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