Acetyl chloride → HCID 9891204, compound

HRID 1354175Notes

Reaction equation

HRID 1354175 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:23][CH:22]=3)=[C:11]3[CH:12]=[CH:13][C:14]([C:16]([F:19])([F:18])[F:17])=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:31](Cl)(=[O:33])[CH3:32]>C(O)(=O)C>[C:31]([NH:30][S:27]([C:24]1[CH:25]=[CH:26][C:21]([C:20]2[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:9][N:10]3[CH:15]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:13]=[CH:12][C:11]=23)=[CH:22][CH:23]=1)(=[O:29])=[O:28])(=[O:33])[CH3:32]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 9845828HCID 9845828, compound

Product 1

HCID 9891204HCID 9891204, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-[2-(3-fluoro-phenyl)-6-trifluoromethyl-pyrazolo[1,5-a]pyridin-3-yl]benzenesulfonamide (0.2 g, 0.46 mmol) and acetyl chloride (Aldrich) (1 ml) in acetic acid (1 ml) was heated at 95° for 1 hr. The solvent was removed and the resulting oil was dissolved in ethyl acetate (30 ml), washed with M Na2CO3 (10 ml) and brine (10 ml). Drying (MgSO4) and removal of solvent gave a white solid which was triturated with 40-60 petroleum ether, filtered and dried to give the title compound (0.17 g 77%). MH− 476

Workup

  1. temperaturewas heated at 95° for 1 hr
  2. customThe solvent was removed
  3. dissolutionthe resulting oil was dissolved in ethyl acetate (30 ml)
  4. washwashed with M Na2CO3 (10 ml) and brine (10 ml)
  5. customDrying
  6. custom(MgSO4) and removal of solvent
  7. customgave a white solid which
  8. customwas triturated with 40-60 petroleum ether
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-696cdde141ac48469dc5fa5139193b62
Source dataset
uspto-grants-2007_05
Patent number
US07223772B1

Reaction notes

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