Imidazole → HCID 57000288, compound

HRID 428303Notes

Reaction equation

HRID 428303 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-1dd33d8b4cdd435e83787a8de95c4ce5
Source dataset
uspto-grants-2001_11
Patent number
US06313180B1

Reaction notes

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