Imidazole → N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(3,4-methylenedioxy)phenoxycarbonyl]-thiophene-3-sulfonamide

HRID 1738499

반응식

HRID 1738499 반응식
C(N1C=CN=C1)(N1C=CN=C1)=O.[Br:13][C:14]1[C:15]([CH3:32])=[N:16][O:17][C:18]=1[NH:19][S:20]([C:23]1[CH:27]=[CH:26][S:25][C:24]=1[C:28]([O:30][CH3:31])=[O:29])(=[O:22])=[O:21].[CH2:33]1[O:37][C:36]2[CH:38]=C(O)[CH:40]=[CH:41][C:35]=2[O:34]1.N1C=CN=C1>C1COCC1>[Br:13][C:14]1[C:15]([CH3:32])=[N:16][O:17][C:18]=1[NH:19][S:20]([C:23]1[CH:27]=[CH:26][S:25][C:24]=1[C:28]([O:30][C:31]1[CH:40]=[CH:41][C:35]2[O:34][CH2:33][O:37][C:36]=2[CH:38]=1)=[O:29])(=[O:21])=[O:22]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 68289SesamolHCID 10833686N-(4-Bromo-3-methyl-5-isoxazolyl)-2-(carbomethoxy)thiophene-3-sulfonamide

생성물 1

HCID 9826741N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(3,4-methylenedioxy)phenoxycarbonyl]-thiophene-3-sulfonamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Carbonyldiimidazole (530 mg., 3.26 mmol.) was added to a solution of N-(4-bromo-3-methyl-5-isoxazolyl)-2-carboxylthiophene-3-sulfonamide (Example 17) (1.0 g, 2.72 mmol) in dry THF (10 ml). The mixture was stirred at room temperature for 15 minutes. Sesamol (767 mg., 5.44 mmol) and imidazole (185 mg, 2.72 mmol) were added simultaneously. The resulting mixture was refluxed for 1 hour and allowed to cool to room temperature. The solvent was evaporated. The residue was partitioned between 1N HCl and EtOAc. The organic layer was dried (MgSO4). The solid was filtered and the filtrate concentrated to give a yellow oil which was recrystalized from EtOAc/Et2O/Hexane. N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(3,4-methylenedioxy)phenoxycarbonyl]-thiophene-3-sulfonamide was obtained as a white powder (494 mg, 37% yield), m.p. 174-176° C.

후처리

  1. temperatureThe resulting mixture was refluxed for 1 hour
  2. temperatureto cool to room temperature
  3. customThe solvent was evaporated
  4. customThe residue was partitioned between 1N HCl and EtOAc
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationThe solid was filtered
  7. concentrationthe filtrate concentrated
  8. customto give a yellow oil which
  9. customwas recrystalized from EtOAc/Et2O/Hexane

출처 및 근거

ORD 기록
ord-dce0c3f44fa54573a9ed85b88e446fdd
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05962490

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