Pyridine → HCID 9945706, compound

HRID 1293131Notes

Reaction equation

HRID 1293131 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[N:13]1[CH:18]=CC=[CH:15][CH:14]=1.[CH3:19][C:20]1[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[C:21]=1[S:28]([C:31]1[N:35]=[CH:34][NH:33][N:32]=1)(=[O:30])=[O:29].CNCC>ClCCl.C(OCC)(=O)C.CCCCCC>[CH3:19][C:20]1[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[C:21]=1[S:28]([C:31]1[N:35]=[CH:34][N:33]([C:5](=[O:11])[N:13]([CH3:18])[CH2:14][CH3:15])[N:32]=1)(=[O:29])=[O:30]

Participants

7

Reactant 4

HCID 1049PyridineHCID 12219N-MethylethylamineHCID 94429TriphosgeneHCID 178425952HCID 178425952, compound

Product 1

HCID 9945706HCID 9945706, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Triphosgene (20 mg) was dissolved in dichloromethane (1 ml). To this solution was added pyridine (0.017 ml) with cooling it on an ice-water bath, and the reaction mixture was stirred for 5 minutes. Then, 3-(2,4,6-trimethylphenyl)sulfonyl-1H-1,2,4-triazole (Example 35-a) (51 mg) was added, and stirred for additional 10 minutes. Then, N-methylethylamine (0.034 ml) was added, and the reaction mixture was stirred at room temperature for 6 hours. The reaction solution was subjected to a silica-gel column chromatography with 50% ethyl acetate/hexane to yield the title compound (52 mg).

Workup

  1. temperaturewith cooling it on an ice-water bath
  2. stirringstirred for additional 10 minutes
  3. stirringthe reaction mixture was stirred at room temperature for 6 hours

Sources & evidence

ORD record
ord-0ca56fe4e04b4403bb4d2ab79a188205
Source dataset
uspto-grants-2007_07
Patent number
US07238720B2

Reaction notes

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