Imidazole → HCID 57000288, compound

HRID 1421558Notes

Reaction equation

HRID 1421558 reaction equation
[CH3:1][N:2]([CH3:23])[N:3]=[C:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:5]12[CH3:6])[C:18]1[CH:17]=[CH:16][C:15]([OH:22])=[CH:14][C:13]=1[CH2:12][CH2:11]3.N1C=CN=C1.[CH3:29][C:30]([Si:33](Cl)([CH3:35])[CH3:34])([CH3:32])[CH3:31].O>CN(C=O)C.CCOCC>[CH3:23][N:2]([CH3:1])[N:3]=[C:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:5]12[CH3:6])[C:18]1[CH:17]=[CH:16][C:15]([O:22][Si:33]([C:30]([CH3:32])([CH3:31])[CH3:29])([CH3:35])[CH3:34])=[CH:14][C:13]=1[CH2:12][CH2:11]3

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 57145367HCID 57145367, compound

Product 1

HCID 57000288HCID 57000288, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 15.5 gr. of 3-hydroxyestra-1,3,5(10)-trien-17-one dimethylhydrazone (34) in 200 ml of DMF was added 13 gr. of imidazole, followed by dropwise addition of 15 gr. of TBDMSCl in 20 ml of ether. After stirring for an additional 16 hr, the reaction mixture was poured onto 2 liters of water and the resulting mixture was stirred for an additional 10 minutes. The precipitate was filtered and dried in vacuo, to provide 20 g of 35, M.p. 100-103° C.

Workup

  1. stirringthe resulting mixture was stirred for an additional 10 minutes
  2. filtrationThe precipitate was filtered
  3. customdried in vacuo

Sources & evidence

ORD record
ord-0cecce0238534b40ac646fefbe587284
Source dataset
uspto-grants-2000_06
Patent number
US06077873

Reaction notes

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