Ethyl 2-aminobenzoate → HCID 898498、化合物

HRID 1084819ノート

反応式

HRID 1084819 の反応式
[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]

参加物

6

反応物 4

HCID 6877Ethyl 2-aminobenzoateHCID 8471TriethylamineHCID 928683-Thiophen-2-ylprop-2-enoic acidHCID 1670692-Chloro-1-methylpyridinium iodide

生成物 1

HCID 898498HCID 898498、化合物収率 45.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-f36049eb20524f8bafa9d902836017b1
出典データセット
uspto-grants-1991_04
特許番号
US05006548

反応ノート

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