Iodine → HCID 15250782, compound

HRID 1447989Notes

Reaction equation

HRID 1447989 reaction equation
[CH3:1][C:2]([C@@H:4]1[C@@:8]2([CH3:23])[CH2:9][CH2:10][C@@H:11]3[C@@:16]4([CH3:22])[CH2:17][CH2:18][C@H:19]([OH:21])[CH2:20][C:15]4=[CH:14][CH2:13][C@H:12]3[C@@H:7]2[CH2:6][CH2:5]1)=[O:3].[I:24]I.[I-].[NH+:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.I.[NH+]1C=CC=CC=1>N1C=CC=CC=1>[I-:24].[OH:21][C@H:19]1[CH2:18][CH2:17][C@@:16]2([CH3:22])[C:15](=[CH:14][CH2:13][C@@H:12]3[C@@H:11]2[CH2:10][CH2:9][C@@:8]2([CH3:23])[C@H:7]3[CH2:6][CH2:5][C@@H:4]2[C:2](=[O:3])[CH2:1][N+:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:20]1

Participants

6

Reactant 4

HCID 807Iodine2×HCID 8955PregnenoloneHCID 20381055HCID 20381055, compoundHCID 2186351518820-83-2

Product 1

HCID 15250782HCID 15250782, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

In a large beaker clamped in an oil bath maintained at 100° C. and containing 100 ml. of pyridine are placed 50 g. of pregnenolone. The beaker is capped with a watch glass and the mixture is stirred until solution is complete. To this mixture is added 43.3 g. of crushed iodine as quickly as possible, and the opaque black-brown solution is quickly stirred to fully dissolve the iodine as much as possible before obvious reaction, and in particular, crystallization begins. Within a few minutes a gentle but brisk reaction begins as indicated by bubbling. Heating is continued for about 1.5 to 2 hours. The reaction mixture is allowed to cool, and the granular reaction product is gently broken up with a spatula and transferred to a sintered glass funnel, crushed to a firm layer, and sucked dry. The beaker is rinsed with pyridine and added to the cake; the cake is resuspended, pressed to a layer again, and sucked dry again. One or two more washes are usually suffient to remove the bulk of contaminating pyridinium hydroiodide present. The cake is now sucked dry under a nitrogen atmosphere to give from 72 g. to 78 g. of the pyridinium iodide compound, having a m.p. of 223°-225° C. Theoretical yield is 83 g. The product is usually contaminated with pyridinium hydroiodide, but since this contaminant does not appear to interfere with the next step, no attempt is made to remove it.

Workup

  1. customIn a large beaker clamped in an oil bath
  2. additioncontaining 100 ml
  3. customThe beaker is capped with a watch glass
  4. additionTo this mixture is added 43.3 g
  5. custompossible before obvious reaction
  6. customin particular, crystallization
  7. customWithin a few minutes a gentle but brisk reaction
  8. customby bubbling
  9. temperatureHeating
  10. temperatureto cool
  11. customtransferred to a sintered glass funnel
  12. customcrushed to a firm layer
  13. customsucked dry
  14. washThe beaker is rinsed with pyridine
  15. additionadded to the cake
  16. customsucked dry again
  17. customto remove the bulk of contaminating pyridinium hydroiodide present
  18. customThe cake is now sucked dry under a nitrogen atmosphere
  19. customto give from 72 g
  20. customto remove it

Sources & evidence

ORD record
ord-e76e03e7caf64b498572f15b63915028
Source dataset
uspto-grants-1979_12
Patent number
US04179453

Reaction notes

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