Sulfuric Acid → HCID 89657495, compound

HRID 930905Notes

Reaction equation

HRID 930905 reaction equation
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

Participants

5

Reactant 4

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

Product 1

HCID 89657495HCID 89657495, compoundYield 63%

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-be7276c92d734293b938a227e594b18a
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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