Ammonium Chloride → 2-Anilino-5-phenylthiophene-3-carboxamide

HRID 1967158노트

반응식

HRID 1967158 반응식
[NH:1]([C:8]1[S:9][C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][C:12]=1[C:13](O)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].C([N:27](CC)C(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C.C(=O)(O)[O-].[Na+].O>[NH:1]([C:8]1[S:9][C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][C:12]=1[C:13]([NH2:27])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

10

반응물 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 582564742-Anilino-5-phenylthiophene-3-carboxylic acid

생성물 1

HCID 446103702-Anilino-5-phenylthiophene-3-carboxamide

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of 2-anilino-5-phenylthiophene-3-carboxylic acid (47.3 mg, 0.160 mmol), ammonium chloride (17.12 mg, 0.320 mmol), and N,N-diisopropylethylamine (0.084 ml, 0.480 mmol) in N,N-dimethylformamide (1 mL) was added 1-hydroxybenzotriazole hydrate (32.4 mg, 0.240 mmol) and then 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (46.0 mg, 0.240 mmol). After being stirred for 15 hours, the reaction mixture was diluted with ethyl acetate (20 mL), saturated aqueous sodium bicarbonate solution (10 mL), and water (2 mL). The layers were separated and the organic layer was washed with water (2×5 mL) and brine (10 mL), dried over sodium sulfate, filtered, and concentrated. The crude reaction mixture was purified by silica gel chromatography (50% ethyl acetate/hexanes) to afford 2-anilino-5-phenylthiophene-3-carboxamide.

후처리

  1. customThe layers were separated
  2. washthe organic layer was washed with water (2×5 mL) and brine (10 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude reaction mixture
  7. customwas purified by silica gel chromatography (50% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-89ad3c9d686d418d836f40f4c8209cbc
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420695B2

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