Dimethylformamide → HCID 85906589, compound

HRID 1510065Notes

Reaction equation

HRID 1510065 reaction equation
CN(C=O)C.[CH2:6]([Cl:8])Cl.P(Cl)(Cl)(Cl)=O.[CH3:14][O:15][C:16]1[CH:24]=[C:23]2[C:19]([CH2:20][C:21](=[O:31])[N:22]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:18][CH:17]=1>C(Cl)(Cl)Cl.N1C=CC=CC=1.CC(=O)OCC>[Cl:8][C:6]1[N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:23]2[C:19]([C:20]=1[CH:21]=[O:31])=[CH:18][CH:17]=[C:16]([O:15][CH3:14])[CH:24]=2

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 12777166HCID 12777166, compound

Product 1

HCID 85906589HCID 85906589, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of DMF (2.1 ml) and DCM (2.1 ml) was cooled to 0° C. and stirred under argon. Within 15 min phosphorus oxychloride (2.1 ml, 22.6 mmol) was added and the reaction mixture was stirred for 30 min at 0° C. The compound of step 1 (550 mg, 2.30 mmol), dissolved in chloroform (5.27 ml) and pyridine (1.05 ml), was then added to the cooled solution. The reaction mixture was stirred at room temperature overnight. The mixture was slowly poured into 300 ml of ice, and after a few minutes EA was added. The organic layer was separated, dried over sodium sulfate, filtered and evaporated under reduced pressure. Column chromatography on silica gel (EA/HEP 1:4) yielded 369 mg of the title compound as a white solid.

Workup

  1. stirringthe reaction mixture was stirred for 30 min at 0° C
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1081d486cfe845438f11d85127696907
Source dataset
uspto-grants-2012_07
Patent number
US08211885B2

Reaction notes

Loading…