Phosphorus oxychloride → HCID 10214620, compound

HRID 1766967Notes

Reaction equation

HRID 1766967 reaction equation
O=P(Cl)(Cl)Cl.O=[C:7]1[CH:13]([NH:14][CH:15]=[O:16])[C:12]2[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=2[S:10][C:9]2[CH:21]=[CH:22][CH:23]=[CH:24][C:8]1=2>C1(C)C=CC=CC=1>[O:16]1[C:7]2[C:8]3[CH:24]=[CH:23][CH:22]=[CH:21][C:9]=3[S:10][C:11]3[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=3[C:13]=2[N:14]=[CH:15]1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 11311722HCID 11311722, compound

Product 1

HCID 10214620HCID 10214620, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of POCl3 (0.137 g, 0.892 mmole) in dry toluene (5 ml), N-(11-oxo-10,11-dihydro-dibenzo[b,f]thiepin-10-yl)-formamide (III; X=S, Y=Z=H. A=NH, R1=H) (0.06 g, 0.223 mmole) dissolved in toluene (10 ml) was added. The reaction mixture was heated under reflux for 2 hours. Then toluene was evaporated to dryness and water was added and it was extracted with ethyl acetate. The organic extract was washed with a saturated NaHCO3 solution and water and dried over anhydrous Na2SO4. The solvent was evaporated and, after purifying by chromatography on a column, an oily product was isolated.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 2 hours
  4. customThen toluene was evaporated to dryness and water
  5. additionwas added
  6. extractionit was extracted with ethyl acetate
  7. extractionThe organic extract
  8. washwas washed with a saturated NaHCO3 solution and water
  9. dry with materialdried over anhydrous Na2SO4
  10. customThe solvent was evaporated
  11. customafter purifying by chromatography on a column
  12. customan oily product was isolated

Sources & evidence

ORD record
ord-8b6364b1500a46c181d8086383e7c647
Source dataset
uspto-grants-2007_06
Patent number
US07232815B2

Reaction notes

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