Potassium Carbonate → HCID 178419912, compound

HRID 1293126Notes

Reaction equation

HRID 1293126 reaction equation
ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[O:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16](O)[CH2:15][CH2:14]1.[SH:24][C:25]1[N:29]=[CH:28][NH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.N1C=CC=CC=1.ClCCl>[O:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]([S:24][C:25]2[N:29]=[CH:28][NH:27][N:26]=2)[CH2:15][CH2:14]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 92890Chroman-4-olHCID 94429TriphosgeneHCID 178527894HCID 178527894, compound

Product 1

HCID 178419912HCID 178419912, compoundYield 47.2%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolvent2×HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of triphosgene (95 mg) and dichloromethane (4 ml), with stirring, were added pyridine (82 μl) and 4-chromanol (150 mg) in this order with cooling it on an ice bath. Additional pyridine (82 μl) was added, and the reaction mixture was stirred at room temperature for 2 hours. The reaction solution was added to a mixture of 3-mercapto-1H-1,2,4-triazole (110 mg), anhydrous potassium carbonate (200 mg) and N,N-dimethylformamide (2 ml), and stirred overnight. The reaction solution was washed with water, followed by saturated aqueous sodium chloride solution, and concentrated. The residue was subjected to a silica-gel column chromatography with 50% ethyl acetate/hexane to yield the title compound (110 mg).

Workup

  1. temperaturewith cooling it on an ice bath
  2. stirringthe reaction mixture was stirred at room temperature for 2 hours
  3. stirringstirred overnight
  4. washThe reaction solution was washed with water
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-347620f152da4b16bd2c6f0d697eaea6
Source dataset
uspto-grants-2007_07
Patent number
US07238720B2

Reaction notes

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