Sulfuric Acid → HCID 86745341, compound

HRID 1461649Notes

Reaction equation

HRID 1461649 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14](C(=O)C)[C:13](=[O:21])[C:12]23[CH2:23][CH2:22]2)[CH:5]=[C:4]([F:24])[C:3]=1[C:25]([F:28])([F:27])[F:26].OS(O)(=O)=O>C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:21])[C:12]23[CH2:22][CH2:23]2)[CH:5]=[C:4]([F:24])[C:3]=1[C:25]([F:28])([F:27])[F:26]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 86745342HCID 86745342, compound

Product 1

HCID 86745341HCID 86745341, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5'-[(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy]-1'-acetyl-spiro[cyclopropane -1,3'-indolin]-2'-one (0.60 g, 1.95 mmol), 5 mL of 1 N H2SO4 and tetrahydrafuran is heated at reflux for about 24 hours (until reaction is complete by gas chromatographic analysis). The reaction mixture is diluted with ethyl acetate and water and the phases are separated. The organic phase is dried (MgSO4) and concentrated in vacuo to give a residue. The residue is chromatographed using silica gel and ethyl acetate/hexane 25/75 to give the title product as a white solid, 0.41 g, (76%), mp 168°-170° C. identified by H1NMR.

Workup

  1. temperatureis heated
  2. temperatureat reflux for about 24 hours
  3. custom(until reaction is complete by gas chromatographic analysis)
  4. customthe phases are separated
  5. dry with materialThe organic phase is dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give a residue
  8. customThe residue is chromatographed

Sources & evidence

ORD record
ord-dee28be70c694cb3bc30adfae3ab62a1
Source dataset
uspto-grants-1991_12
Patent number
US05076835

Reaction notes

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