Ethyl 2-aminobenzoate → HCID 898498, 화합물

HRID 1084819노트

반응식

HRID 1084819 반응식
[I-].ClC1C=CC=C[N+]=1C.[S: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>[S: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 928683-Thiophen-2-ylprop-2-enoic acidHCID 1670692-Chloro-1-methylpyridinium iodide

생성물 1

HCID 898498HCID 898498, 화합물수율 45.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

Under nitrogen stream, 2-chloro-1-methylpyridinium iodide (966 mg, 3.89 mmol) was suspended in dry methylene chloride (5 ml). To the suspension, a solution of 3-(2-thienyl)acrylic acid (500 mg, 3.24 mmol), triethylamine (1.08 ml, 7.78 mmol), and ethyl 2-aminobenzoate (0.48 ml, 3.24 mmol) in dry methylene chloride (5 ml) was added dropwise. After the addition, the mixture was heated under reflux for 39 hours. Then, the reaction mixture was diluted with methylene chloride, 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 yellow solid, which was washed with n-hexane to give pale yellow solids of the title compound (442 mg, yield, 45%). m.p., 126°-127° C. (recrystallized from methanol)

후처리

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 39 hours
  4. washwashed with 10% aqueous HCl, saturated aqueous sodium chloride, 1N-aqueous NaOH, and saturated aqueous sodium chloride successively
  5. customdried
  6. customRemoval of solvent
  7. customgave a yellow solid, which
  8. washwas washed with n-hexane

출처 및 근거

ORD 기록
ord-f36049eb20524f8bafa9d902836017b1
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05006548

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