Imidazole → HCID 59410206, compound

HRID 85215Notes

Reaction equation

HRID 85215 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:5](=[O:22])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=2[CH2:19][O:20][CH3:21])[CH:7]=[CH:8][CH:9]=1.N1C=CN=C1.[C:28]([Si:32]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)Cl)([CH3:31])([CH3:30])[CH3:29]>CN(C)C=O>[Si:32]([O:1][CH2:2][CH2:3][C:4]1[C:5](=[O:22])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=2[CH2:19][O:20][CH3:21])[CH:7]=[CH:8][CH:9]=1)([C:28]([CH3:31])([CH3:30])[CH3:29])([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 59410166HCID 59410166, compound

Product 1

HCID 59410206HCID 59410206, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20 g (65 mmol) of the compound from Example 30A are dissolved in 75 ml of anhydrous N,N-dimethylformamide, and, with ice-cooling, first 5.3 g (78 mmol) of imidazole and then, a little at a time over a period of 3 min, 19 g (72 mmol) of tert-butyldiphenylchlorosilane are added. Cooling is removed, and the mixture is stirred at room temperature for a further 19 h. The reaction solution is diluted with ethyl acetate and washed three times with water and twice with saturated sodium chloride solution. The mixture is then dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure. tert-Butyl methyl ether is added to the residue, and the resulting crystals are filtered off and dried under reduced pressure. This gives 39 g (90% of theory) of the desired product.

Workup

  1. temperaturewith ice-cooling
  2. temperatureCooling
  3. customis removed
  4. additionThe reaction solution is diluted with ethyl acetate
  5. washwashed three times with water
  6. dry with materialThe mixture is then dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure
  9. additiontert-Butyl methyl ether is added to the residue
  10. filtrationthe resulting crystals are filtered off
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-cc7e3764b52443d79271c372f059d337
Source dataset
uspto-grants-2014_09
Patent number
US08846934B2

Reaction notes

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