Imidazole → HCID 11756635, compound

HRID 1884879Notes

Reaction equation

HRID 1884879 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH2:8][CH2:9][O:10][C:11]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[S:16][C:15]=2[C:14]([OH:26])=[CH:13][CH:12]=1)[CH2:5][CH2:6][Cl:7].[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].N1C=CN=C1.CN(C1C=CC=CN=1)C>CN(C)C=O.O>[Cl:1][CH2:2][CH2:3][N:4]([CH2:8][CH2:9][O:10][C:11]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[S:16][C:15]=2[C:14]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])=[CH:13][CH:12]=1)[CH2:5][CH2:6][Cl:7]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 218852-DimethylaminopyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 11961976HCID 11961976, compound

Product 1

HCID 11756635HCID 11756635, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 0.50 g of 1-(N,N-bischloroethylaminoethoxy)-4-hydroxythioxanthone in 10 ml of dimethylformamide is mixed with 0.22 g of tert-butyldimethylsilyl chloride, 0.20 g of imidazole and a catalytic amount of dimethylaminopyridine, and stirred at room temperature for 12 h. The solution is then added over water and extracted with ethyl acetate. The ethyl acetate extract is washed sequentially with saturated sodium bicarbonate and water, dried over sodium sulfate, concentrated and dissolved in a mixture of ethyl acetate: hexanes (1:4) and passed through a plug of alumina. The solid obtained after concentration is pure and weighed 0.48 g (70%).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washis washed sequentially with saturated sodium bicarbonate and water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. dissolutiondissolved in a mixture of ethyl acetate: hexanes (1:4)
  7. customThe solid obtained
  8. concentrationafter concentration

Sources & evidence

ORD record
ord-92fca7d24881490ab7064e186201945b
Source dataset
uspto-grants-2004_07
Patent number
US06767919B2

Reaction notes

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