Phosphorus oxychloride → HCID 18545346, compound

HRID 1267084Notes

Reaction equation

HRID 1267084 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15]/[CH:16]=[CH:17]/[C:18]3[CH:19]=[N:20][N:21]([C:24]4[CH:29]=[C:28]([CH3:30])[N:27]=[C:26](O)[N:25]=4)[C:22]=3[CH3:23])[CH2:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.P(Cl)(Cl)([Cl:34])=O>>[Cl:34][C:26]1[N:25]=[C:24]([N:21]2[C:22]([CH3:23])=[C:18](/[CH:17]=[CH:16]/[CH2:15][N:12]3[CH2:13][CH2:14][N:9]([C:4]4[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=4)[CH2:10][CH2:11]3)[CH:19]=[N:20]2)[CH:29]=[C:28]([CH3:30])[N:27]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178428093HCID 178428093, compound

Product 1

HCID 18545346HCID 18545346, compound

Conditions

Temperature
60 °C

Procedure

To 250 mg of the compound obtained in Example 34 was added 5 ml of phosphorus oxychloride. The mixture was stirred at 60° C. for 2.5 hours, followed by concentration. A mixture of the concentrate and water was neutralized with sodium hydrogencarbonate and extracted with chloroform three times. The combined organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was subjected to silica gel column chromatography using chloroform was a developing solution. Concentration of the fraction containing the desired compound gave 180 mg of the title compound.

Workup

  1. concentrationfollowed by concentration
  2. additionA mixture of the
  3. concentrationconcentrate
  4. extractionextracted with chloroform three times
  5. washThe combined organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. additionConcentration of the fraction containing the desired compound

Sources & evidence

ORD record
ord-908cee85c1d040568c72ff4e96269336
Source dataset
uspto-grants-2003_04
Patent number
US06552018B1

Reaction notes

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