Sulfuric Acid → HCID 89657495, 화합물

HRID 930905노트

반응식

HRID 930905 반응식
C([N:8]1[C:12]2[C:13](=[O:37])[N:14]([CH3:36])[CH:15]=[C:16]([C:17]3[CH:22]=[C:21]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:20]=[CH:19][C:18]=3[O:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=3[F:35])[C:11]=2[CH:10]=[C:9]1[C:38]([O:40][CH2:41][CH3:42])=[O:39])C1C=CC=CC=1.C1(OC)C=CC=CC=1.S(=O)(=O)(O)O.FC(F)(F)C(O)=O>>[F:35][C:29]1[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:28]=1[O:27][C:18]1[CH:19]=[CH:20][C:21]([S:23]([CH3:26])(=[O:24])=[O:25])=[CH:22][C:17]=1[C:16]1[C:11]2[CH:10]=[C:9]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[NH:8][C:12]=2[C:13](=[O:37])[N:14]([CH3:36])[CH:15]=1

참가 물질

5

반응물 4

HCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 89657630HCID 89657630, 화합물

생성물 1

HCID 89657495HCID 89657495, 화합물수율 63%

실험 절차

A mixture of Example 252e, anisole (1.585 mL, 14.51 mmol) and concentrated sulfuric acid (4.3 mL, 81 mmol) in trifluoroacetic acid (20 mL, 260 mmol) was heated at 90° C. for 4 hours. Excess trifluoroacetic acid was removed under reduced pressure, and the residue was partitioned between water (100 mL) and ethyl acetate (200 mL). The organic layer was separated, and the aqueous layer was extracted with additional ethyl acetate (2×200 mL). The combined organic layers were washed with saturated aqueous sodium bicarbonate (100 mL), followed by saturated aqueous sodium chloride (100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was taken into methanol (50 mL) and the resulting solid was filtered, rinsed with methanol, and dried to provide the title compound (3.1 g, 63% yield).

후처리

  1. customExcess trifluoroacetic acid was removed under reduced pressure
  2. customthe residue was partitioned between water (100 mL) and ethyl acetate (200 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with additional ethyl acetate (2×200 mL)
  5. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate (100 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. filtrationthe resulting solid was filtered
  10. washrinsed with methanol
  11. customdried

출처 및 근거

ORD 기록
ord-be7276c92d734293b938a227e594b18a
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296741B2

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