Phosphoric Acid → HCID 66922272, compound

HRID 2039866Notes

Reaction equation

HRID 2039866 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1)[CH3:2].ClN1C(=[O:25])CCC1=O.P(=O)(O)(O)O>C(Cl)Cl.O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:11](=[O:25])[CH2:10][C:7]2=[N:8][CH:9]=1)[CH3:2]

Participants

6

Reactant 3

HCID 1004Phosphoric AcidHCID 31398ChlorosuccinimideHCID 66922323HCID 66922323, compound

Product 1

HCID 66922272HCID 66922272, compoundYield 29.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The compound of step 3 (2.05 g, 8.60 mmol) was dissolved in DCM (30 ml) and N-chlorosuccinimide (1.26 g, 9.46 mmol) was added. The reaction mixture was stirred at room temperature for 3 days. The solvent was removed, and the obtained solid was dissolved in acetic acid (10 ml) and heated to 70° C. After addition of phosphoric acid (7.31 ml, 107 mmol, 85%), the reaction mixture was heated to 120° C. for 3 days. After cooling, the mixture was diluted with water and extracted with EA. The extracts were dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (EA/HEP 1:6). 650 mg of the title compound were obtained.

Workup

  1. customThe solvent was removed
  2. dissolutionthe obtained solid was dissolved in acetic acid (10 ml)
  3. temperatureheated to 70° C
  4. temperaturethe reaction mixture was heated to 120° C. for 3 days
  5. temperatureAfter cooling
  6. extractionextracted with EA
  7. dry with materialThe extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by silica gel chromatography (EA/HEP 1:6)

Sources & evidence

ORD record
ord-cb3955651e3b41aba5101f3a101674e3
Source dataset
uspto-grants-2013_11
Patent number
US08580813B2

Reaction notes

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