2,3-Dichloropyrazine → HCID 90303493, 화합물

HRID 62453

반응식

HRID 62453 반응식
C(/[N:14]=[CH:15]/[C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:36][C:37]1[C:42](Cl)=[N:41][CH:40]=[CH:39][N:38]=1>C1COCC1>[NH2:14][CH:15]([C:42]1[C:37]([Cl:36])=[N:38][CH:39]=[CH:40][N:41]=1)[C:16]1[CH:17]=[CH:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:24][CH:25]=1

참가 물질

5

반응물 3

HCID 785752,3-DichloropyrazineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 178497919HCID 178497919, 화합물

생성물 1

HCID 90303493HCID 90303493, 화합물수율 81.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of (E)-methyl 4-((benzhydrylimino)methyl)benzoate (67 g, 204 mmol) in THF (700 mL) was cooled to 0° C. and added dropwise NaHMDS (244 mL, 244 mmol). The mixture was stirred at this temperature for 30 minutes, and added a solution of 2,3-dichloropyrazine (33.2 g, 224 mmol) in THF (40 mL). The reaction mixture was stirred at 0° C. for 20 minutes and RT for 40 minutes. After the reaction was completed, the reaction mixture was extracted with EA and water. The organic layer was treated with 3M HCl (500 mL) for 10 minutes. The phases were separated and the organic layer was extracted with 3M HCl. The aqueous was washed with EA and then alkalified with Na2CO3 to pH=9. The aqueous solution was extracted with EA and the combined organics were dried and concentrated to give methyl 4-(amino(3-chloropyrazin-2-yl)methyl)benzoate (46 g, yield 81%).

후처리

  1. stirringThe reaction mixture was stirred at 0° C. for 20 minutes and RT for 40 minutes
  2. extractionthe reaction mixture was extracted with EA and water
  3. additionThe organic layer was treated with 3M HCl (500 mL) for 10 minutes
  4. customThe phases were separated
  5. extractionthe organic layer was extracted with 3M HCl
  6. washThe aqueous was washed with EA
  7. extractionThe aqueous solution was extracted with EA
  8. customthe combined organics were dried
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f78ef12cdd7844ecb1edb41d70388ec3
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09446130B2

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