Imidazole → HCID 54166792, compound

HRID 1003147Notes

Reaction equation

HRID 1003147 reaction equation
[C:1]([C:3]1[S:4][C:5]2[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].N1C=CN=C1.[C:18]([Si:22]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)Cl)([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C.C(OCC)(=O)C>[C:1]([C:3]1[S:4][C:5]2[CH:11]=[C:10]([O:12][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 98819122-Cyano-6-hydroxybenzothiazole

Product 1

HCID 54166792HCID 54166792, compoundYield 112%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-cyano-6-hydroxybenzothiazole (5.0 g, 28 mmol) in 100 ml of anhydrous DMF under inert atmosphere was treated with 2.9 g of imidazole (4.2 mmol) followed by t-butyldiphenylchlorosilane (9.34 g, 34 mmol). The reaction was stirred at room temperature for 3 h and then diluted with 200 ml of ethyl acetate and washed with water (4×400 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography, eluting with 5-10% ethyl acetate/hexanes to afford 13.0 g of the desired product containing ~10% silyl impurity in quantitative yield. The product was taken on without further purification. 1H NMR (CDCl3): δ 1.12 (s, 9H) ; 7.13-7.46 (m, 8H); 7.70-7.72 (m, 4H); 7.92-7.95 (d, 1H).

Workup

  1. washwashed with water (4×400 ml)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by column chromatography
  5. washeluting with 5-10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-824dca40d2524dcdba74a09273f3664d
Source dataset
uspto-grants-2000_04
Patent number
US06045991

Reaction notes

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