Sodium Azide → HCID 13714626, compound

HRID 845209Notes

Reaction equation

HRID 845209 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+]=[N-].[Na+]>CN(C)C=O.O>[NH2:23][C:18]1[C:17](=[O:20])[CH2:16][CH2:15][C@@:14]2([CH3:21])[C:19]=1[CH:2]=[CH: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]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 53867648HCID 53867648, compound

Product 1

HCID 13714626HCID 13714626, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

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 dissolved in 2 ml of water. The resulting mixture is heated at 100° C. for 90 minutes, cooled and worked up as described in the example 1. There are obtained 0.325 g of the title compound, m.p. 148°-150° C. (dec.).

Workup

  1. temperaturecooled

Sources & evidence

ORD record
ord-10c04ded3649472399c52adf089aa364
Source dataset
uspto-grants-1988_07
Patent number
US04757061

Reaction notes

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