Sodium Azide → HCID 131715974, compound

HRID 1905009Notes

Reaction equation

HRID 1905009 reaction equation
Br[C@H:2]1[C:19]2[C@:14]([CH3:22])([CH:15]3[CH2:21][C@@H:16]3[C:17](=[O:20])[CH:18]=2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:23])[CH2:7][CH2:6]3)[CH2:3]1.[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C)C=O>[N:24]([C@@H:2]1[C:19]2[C@:14]([CH3:22])([CH:15]3[CH2:21][C@@H:16]3[C:17](=[O:20])[CH:18]=2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:23])[CH2:7][CH2:6]3)[CH2:3]1)=[N+:25]=[N-:26]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 70395582HCID 70395582, compound

Product 1

HCID 131715974HCID 131715974, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6β-bromo-1,2β-methylenandrost-4-ene-3,17-dione (378 mg, 1 mmol), sodium azide (66 mg, 1 mmol) and dimethylformamide (10 ml) is heated from 20° to 100° C. Then the reaction mixture is cooled, poured onto ice water and extracted with ethyl acetate. The organic layer is separated, washed with water, dried and evaporated in vacuo. Purification is achieved by column chromatography over silica gel eluting with benzene/ether to yield pure 6α-azido-1,2β-methylenandrost-4-ene-3,17-dione (238 mg, 70%). Found: C 70.61, H 7.35, N 12.27. C20H25N3O2 requires: C 70.77, H 7.12, N, 12.38.

Workup

  1. temperatureis heated from 20° to 100° C
  2. temperatureThen the reaction mixture is cooled
  3. additionpoured onto ice water
  4. extractionextracted with ethyl acetate
  5. customThe organic layer is separated
  6. washwashed with water
  7. customdried
  8. customevaporated in vacuo
  9. customPurification

Sources & evidence

ORD record
ord-9ddc427aa5594319be916c1fe5180093
Source dataset
uspto-grants-1989_06
Patent number
US04840943

Reaction notes

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