Hydrochloric Acid → HCID 12796455, compound

HRID 2049471Notes

Reaction equation

HRID 2049471 reaction equation
N(=C([C:5]1[C@:22]2([CH3:23])[C@H:8]([C@H:9]3[C@H:19]([C:20](=[O:24])[CH2:21]2)[C@:17]2([CH3:18])[C@H:12]([CH2:13][CH:14]=[CH:15][CH2:16]2)[CH2:11][CH2:10]3)[CH2:7][CH:6]=1)C)O.P(Cl)(Cl)(Cl)=[O:26].Cl>N1C=CC=CC=1.O>[CH3:23][C@:22]12[CH2:21][C:20](=[O:24])[C@H:19]3[C@@H:9]([CH2:10][CH2:11][C@@H:16]4[C@:17]3([CH3:18])[CH2:12][CH:13]=[CH:14][CH2:15]4)[C@@H:5]1[CH2:6][CH2:7][C:8]2=[O:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 86736925HCID 86736925, compound

Product 1

HCID 12796455HCID 12796455, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent2×

Procedure

A solution of 20-oximino-5α-pregna-2,16-diene-11-one (60 g) in anhydrous pyridine (250 ml) was treated with 225 ml of a solution prepared from phosphorus oxychloride (55 ml) in anhydrous pyridine (250 ml) whilst maintaining the reaction temperature at `5° during addition of the reagent. The reaction mixture was then added to a solution of concentrated HCl (350 ml) in water (3 l). This mixture was stirred for 60 hours before collecting the precipitate by filtration. The precipitate was washed with water, dissolved in hot industrial methylated spirits and treated with 2 N HCl (50 ml) at room temperature. After one hour, the reaction mixture was diluted with water and the precipitate obtained was collected by filtration, washed with water and dried. (38.4 g). Crystallisation from methanol afforded the title compound, m.p. 188°-192°, [α]D +207°.

Workup

  1. temperaturewhilst maintaining the reaction temperature at `5°
  2. additionduring addition of the reagent
  3. custombefore collecting the precipitate
  4. filtrationby filtration
  5. washThe precipitate was washed with water
  6. dissolutiondissolved in hot industrial methylated spirits
  7. additiontreated with 2 N HCl (50 ml) at room temperature
  8. waitAfter one hour
  9. additionthe reaction mixture was diluted with water
  10. customthe precipitate obtained
  11. filtrationwas collected by filtration
  12. washwashed with water
  13. customdried
  14. customCrystallisation from methanol

Sources & evidence

ORD record
ord-5a985af93f394809aa9f144bb5a21303
Source dataset
uspto-grants-1980_04
Patent number
US04197296

Reaction notes

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