Methanol → HCID 13714628, compound

HRID 845210Notes

Reaction equation

HRID 845210 reaction equation
Br[CH:2]1[C:19]2[C@:14]([CH3:21])([CH2:15][CH2:16][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:22])[CH2:7][CH2:6]3)[CH2:3]1.[N-:23]=[N+:24]=[N-:25].[Na+].CO>CN(C)C=O>[N:23]([C:18]1[C:17](=[O:20])[CH2:16][CH2:15][C@@:14]2([CH3:21])[C:19]=1[CH2:2][CH2:3][C@@H:4]1[C@@H:13]2[CH2:12][CH2:11][C@@:9]2([CH3:10])[C@H:5]1[CH2:6][CH2:7][C:8]2=[O:22])=[N+:24]=[N-:25]

Participants

5

Reactant 3

HCID 887MethanolHCID 33557Sodium AzideHCID 53867648HCID 53867648, compound

Product 1

HCID 13714628HCID 13714628, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1.1 g of 6-bromoandrost-4-en-3,17-dione in 57.4 ml of dimethylformamide are added 0.250 g of sodium azide. The resulting mixture is heated at 30°-35° C. for 72 hours, cooled and worked up as described in the example 3. There are obtained 0.476 g of the title compound, m.p. (MeOH) 143°-144° C. (dec.);

Workup

  1. temperatureThe resulting mixture is heated at 30°-35° C. for 72 hours
  2. temperaturecooled

Sources & evidence

ORD record
ord-866ff1589ef345e38871e84e5d9ef043
Source dataset
uspto-grants-1988_07
Patent number
US04757061

Reaction notes

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