Acetyl chloride → HCID 15870959, compound

HRID 29040Notes

Reaction equation

HRID 29040 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]([C:18]3[CH:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)[CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:13]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:28](Cl)(=[O:30])[CH3:29]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]([C:18]3[CH:19]=[CH:20][C:21]([S:24]([NH:27][C:28](=[O:30])[CH3:29])(=[O:26])=[O:25])=[CH:22][CH:23]=3)[CH:11]=[C:12]([C:14]([F:16])([F:15])[F:17])[N:13]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 22643554HCID 22643554, compound

Product 1

HCID 15870959HCID 15870959, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 4-[2-(3-chloro-5-methylphenyl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide (0.30 g, 0.72 mmol) in 1.5 mL of acetic acid was added 1.5 mL of acetyl chloride at room temperature. The mixture was heated at reflux for 5 hours. After cooling, the reaction mixture was concentrated under vacuum and the residue was treated with ether to give 0.23 g (70%) of N-[[4-[2-(3-chloro-5-methylphenyl)-4-(trifluoromethyl)-1H-imidazol-1-yl]phenyl]sulfonyl]acetamide as a white solid: mp (DSC) 232-235° C. Anal. Calc'd. for C19H15ClF3N3O3S: C, 49.84; H, 3.30; N, 9.18; S, 7.00. Found: C, 49.72; H, 3.48; N, 8.81; S, 7.18.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated under vacuum
  5. additionthe residue was treated with ether

Sources & evidence

ORD record
ord-e1728cfbdd74421281a7f43f51d3532e
Source dataset
uspto-grants-2008_09
Patent number
US07420061B2

Reaction notes

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