Water → 1-Methanesulfonyl-4-nitro-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 2249508노트

반응식

HRID 2249508 반응식
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)=[O:5])[CH3:2].[H-].[Na+].[CH3:16][S:17](Cl)(=[O:19])=[O:18].O>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]([S:17]([CH3:16])(=[O:19])=[O:18])[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)=[O:5])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 242169Ethyl 4-Nitropyrrole-2-carboxylate

생성물 1

HCID 596396991-Methanesulfonyl-4-nitro-1H-pyrrole-2-carboxylic acid ethyl ester수율 84.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-nitro-1H-pyrrole-2-carboxylic acid ethyl ester (2.0 g, 10.86 mmol) in anhydrous THF (54 mL) was added NaH (650 mg, 60% dispersion, 16.25 mmol) at room temperature. The suspension was stirred at room temperature for 30 minutes before the addition of methanesulfonyl chloride (1.87 g, 16.32 mmol). The reaction mixture was stirred at room temperature over night. Water was carefully added to the reaction solution, and the resulting mixture was extracted with EtOAc (3×50 mL). The combined organic layers were washed with aqueous NaHCO3 solution and brine, dried over MgSO4, filtered, and evaporated under reduced pressure to give a white solid (2.4 g, 84%). The crude product was used directly without purification. 1H NMR (500 MHz, DMSO-d6) δ8.36 (s, 1H), 7.60 (s, 1H), 4.33 (q, 2H), 4.02 (s, 3H), 2.51 (DMSO), 1.35 (t, 3H) ppm. MS (ES−): m/e=183.1 (M−Ms); LC/Method A/3.64 min.

후처리

  1. extractionthe resulting mixture was extracted with EtOAc (3×50 mL)
  2. washThe combined organic layers were washed with aqueous NaHCO3 solution and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-36c8e5179c8f4d5a87b7444471b64d19
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07314885B2

반응 노트

불러오는 중…