Thiourea → 6-(5-Cholesten-3beta-yloxy)-hexane-1-thiol

HRID 903978Notes

Reaction equation

HRID 903978 reaction equation
N[C:2](N)=[S:3].[CH3:5][CH:6]([CH2:8][CH2:9][CH2:10][C@H:11]([C@@H:13]1[C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C@H:27]([CH2:28][CH2:29]2)[C@:25]2([CH3:26])[C:20]([CH2:21][C@@H:22]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]CI)[CH2:23][CH2:24]2)=[CH:19][CH2:18]3)[CH2:15][CH2:14]1)[CH3:12])[CH3:7]>O1CCCC1>[CH3:7][CH:6]([CH2:8][CH2:9][CH2:10][C@H:11]([C@@H:13]1[C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C@H:27]([CH2:28][CH2:29]2)[C@:25]2([CH3:26])[C:20]([CH2:21][C@@H:22]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:2][SH:3])[CH2:23][CH2:24]2)=[CH:19][CH2:18]3)[CH2:15][CH2:14]1)[CH3:12])[CH3:5]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 128055256-(5-Cholesten-3beta-yloxy)hexyl iodide

Product 1

HCID 867372786-(5-Cholesten-3beta-yloxy)-hexane-1-thiolYield 86.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Thiourea (7.5 g) is added to a solution of 6-(5-cholesten-3β-yloxy)hexyl iodide (15 g, 25.3 mmol) in tetrahydrofuran (200 ml) and the mixture is heated with stirring under reflux for 6 hours. The solution is concentrated to a residue which is triturated with anhydrous ether. The solid is filtered and dissolved in chloroform (100 ml). This solution is added to a solution of potassium metabisulfite (15 g) in water (100 ml). The mixture is heated under reflux in a nitrogen atmosphere for 20 minutes. The organic layer is washed with water, dried, and concentrated to dryness. The crude material is put on a silica gel column and eluted with 5% ethyl ether in peteroleum ether. The dried fractions are pooled and concentrated to give the title compound (11 g, 86% yield), m.p. 89°-90°.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 6 hours
  3. concentrationThe solution is concentrated to a residue which
  4. customis triturated with anhydrous ether
  5. filtrationThe solid is filtered
  6. dissolutiondissolved in chloroform (100 ml)
  7. additionThis solution is added to a solution of potassium metabisulfite (15 g) in water (100 ml)
  8. temperatureThe mixture is heated
  9. temperatureunder reflux in a nitrogen atmosphere for 20 minutes
  10. washThe organic layer is washed with water
  11. customdried
  12. concentrationconcentrated to dryness
  13. washeluted with 5% ethyl ether in peteroleum ether
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-2f08834b8f5742f181bb8cb76eba6172
Source dataset
uspto-grants-1980_10
Patent number
US04229441

Reaction notes

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