Hydrochloric Acid → HCID 131715879, compound

HRID 1193468Notes

Reaction equation

HRID 1193468 reaction equation
[CH2:1]1[C@@H:3]2[C:4](=[O:23])[CH:5]3O[C:6]43[C@:19]([CH3:20])([CH:2]12)[C@@H:18]1[C@H:9]([C@H:10]2[C@@:14]([CH2:16][CH2:17]1)([CH3:15])[C:13](=[O:21])[CH2:12][CH2:11]2)[CH2:8][CH2:7]4.S(=O)(=O)(O)O.[N-:29]=[N+:30]=[N-:31].[Na+].Cl>CS(C)=O.O>[CH2:1]1[C@@H:3]2[C:4](=[O:23])[C:5]([N:29]=[N+:30]=[N-:31])=[C:6]3[C@:19]([CH3:20])([CH:2]12)[C@@H:18]1[C@H:9]([C@H:10]2[C@@:14]([CH2:16][CH2:17]1)([CH3:15])[C:13](=[O:21])[CH2:12][CH2:11]2)[CH2:8][CH2:7]3

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 88626626HCID 88626626, compound

Product 1

HCID 131715879HCID 131715879, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 1,2β-methylen-4,5-epoxyandrostane-3,17-dione (0.50 g, 1.59 mmole) in dry dimethylsulfoxide (7.5 ml) is added conc. sulfuric acid (0.11 ml) and sodium azide (1.4 g). The resulting reaction mixture is heated at about 85° C. during 3 hours, cooled, poured into a mixture of water (50 ml) and conc. hydrochloric acid (4 ml), and extracted with ethyl acetate (3×50 ml). The combined organic extracts are dried over sodium sulfate, filtered and evaporated in vacuo to yield a solid which is purified by flash column chromatography eluting with n-hexane-diethyl ether 6:4. There are obtained 0.378 g (70% yield) of 1,2β-methylen-4-azidoandrost-4-ene-3,17-dione [I, R=--N, R1 =R2 =H; (a) and (b)=single bonds]

Workup

  1. customThe resulting reaction mixture
  2. temperaturecooled
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. dry with materialThe combined organic extracts are dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto yield a solid which
  8. customis purified by flash column chromatography
  9. washeluting with n-hexane-diethyl ether 6:4

Sources & evidence

ORD record
ord-17c3624faf144df9b62c3c1d43937220
Source dataset
uspto-grants-1989_03
Patent number
US04810423

Reaction notes

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