Ammonium Chloride → HCID 67029513, 화합물

HRID 1465447노트

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HRID 1465447 반응식
[Cl-].[C:2]([O:6][C:7]([NH:9][NH:10][C:11]([CH2:13][C:14]1[CH:39]=[CH:38][C:17]([CH2:18][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:16][CH:15]=1)=[O:12])=[O:8])([CH3:5])([CH3:4])[CH3:3].C([Li])CCC.[CH:45]([C:47]1[S:51][C:50]([NH:52][C:53](=[O:55])[CH3:54])=[CH:49][CH:48]=1)=O.[Cl-].[NH4+]>O1CCCC1>[C:53]([NH:52][C:50]1[S:51][C:47]([CH:45]=[CH:18][C:17]2[CH:16]=[CH:15][C:14]([CH2:13][C:11]([NH:10][NH:9][C:7]([O:6][C:2]([CH3:3])([CH3:4])[CH3:5])=[O:8])=[O:12])=[CH:39][CH:38]=2)=[CH:48][CH:49]=1)(=[O:55])[CH3:54]

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 268899N-(5-Formyl-2-thienyl)acetamideHCID 86651838HCID 86651838, 화합물HCID 178418339Butyllithium

생성물 1

HCID 67029513HCID 67029513, 화합물수율 28%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

{4-[2-(tert-Butoxycarbonyl)hydrazinocarbonylmethyl]benzyl}(triphenyl)phosphonium chloride (2.97 g, 5.29 mmol) was suspended in anhydrous tetrahydrofuran (8 ml), and cooled to −78° C. n-Butyllithium (1.6M-hexane solution, 3.3 ml, 5.3 mmol) was added dropwise, and the mixture was stirred at −78° C. for 15 mins and at 0° C. for 2 hrs. A solution of N-(5-formylthiophen-2-yl)acetamide (280 mg, 1.65 mmol) in anhydrous tetrahydrofuran (2 ml) was added dropwise, and the mixture was warmed to room temperature. After stirring at room temperature overnight, saturated aqueous ammonium chloride solution was added. The mixture was extracted with dichloromethane and the combined organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (dichloromethane:methanol=97:3→80:20) to give tert-butyl 2-({4-[2-(5-acetylaminothiophen-2-yl)vinyl]phenyl}acetyl)hydrazinecarboxylate (192 mg, yield 28%, E/Z mixture) as a yellow solid.

후처리

  1. additionwas added dropwise
  2. temperaturethe mixture was warmed to room temperature
  3. stirringAfter stirring at room temperature overnight
  4. extractionThe mixture was extracted with dichloromethane
  5. washthe combined organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=97:3→80:20)

출처 및 근거

ORD 기록
ord-774ebe64261c4fa0b72d0bc9e2d0b9f1
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999989B2

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