Diethyl chlorophosphate → HCID 10097974, compound

HRID 1987187Notes

Reaction equation

HRID 1987187 reaction equation
[Na+].[Cl:2][C:3]1[N:4]=[CH:5][N:6]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([NH-:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][CH:9]=1.[P:27](Cl)([O:32][CH2:33][CH3:34])([O:29][CH2:30][CH3:31])=[O:28]>C1COCC1>[Cl:2][C:3]1[N:4]=[CH:5][N:6]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([NH:26][P:27](=[O:28])([O:32][CH2:33][CH3:34])[O:29][CH2:30][CH3:31])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[C:7]=1[C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH3:16])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 13139Diethyl chlorophosphateHCID 131727498HCID 131727498, compound

Product 1

HCID 10097974HCID 10097974, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-[4-chloro-5-(4-ethoxyphenyl)imidazol-1-yl]benzenesulfonamide sodium salt (2.89 mmol) (obtained in the preceding section) in THF (12 mL), diethyl chlorophosphate (0.42 mL, 2.89 mmol) was added under argon atmosphere. The resulting solution was stirred at room temperature for 15 days. It was then concentrated to dryness and the resulting residue was partitioned between H2O and EtOAc, the suspension was filtered and the phases separated. The organic phase was dried and concentrated to afford a solid which was purified by chromatography on silica gel using mixtures hexane/EtOAc and EtOAc/MeOH of increasing polarity as eluent. The product obtained was then recrystallized from ACN to afford the title compound of the example as a yellowish solid (15% yield).

Workup

  1. concentrationIt was then concentrated to dryness
  2. customthe resulting residue was partitioned between H2O and EtOAc
  3. filtrationthe suspension was filtered
  4. customthe phases separated
  5. customThe organic phase was dried
  6. concentrationconcentrated
  7. customto afford a solid which
  8. customwas purified by chromatography on silica gel using mixtures hexane/EtOAc and EtOAc/MeOH
  9. temperatureof increasing polarity as eluent
  10. customThe product obtained
  11. customwas then recrystallized from ACN

Sources & evidence

ORD record
ord-f1b7342d458b415cb31cc558ff588653
Source dataset
uspto-grants-2009_06
Patent number
US07550497B2

Reaction notes

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