1,1'-Carbonyldiimidazole → HCID 67060847, compound

HRID 1186080Notes

Reaction equation

HRID 1186080 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[C:5]([NH2:20])=[CH:4][CH:3]=1.[C:21](N1C=CN=C1)(N1C=CN=C1)=[O:22]>C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:20][C:21](=[O:22])[N:8]([CH2:9][CH2:10][CH2:11][O:12][Si:13]([C:16]([CH3:17])([CH3:19])[CH3:18])([CH3:14])[CH3:15])[C:6]=2[CH:7]=1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 70664257HCID 70664257, compound

Product 1

HCID 67060847HCID 67060847, compoundYield 57.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Bromo-N1-(3-((tert-butyldimethylsilyl)oxy)propyl)benzene-1,2-diamine (1.8 g, 5.14 mmol) was dissolved in dry THF (50 mL) and 1,1′-carbonyl-diimidazole (0.92 g, 5.65 mmol) was added. The dark brown solution was stirred at room temperature under nitrogen overnight. The mixture was diluted with ethyl acetate and washed with water then brine and dried over anhydrous magnesium sulfate. After filtration and concentration the crude product was chromatographed on silica gel eluting with 5-50% ethyl acetate in hexanes to give 6-bromo-1-(3-((tert-butyldimethylsilyl)oxy)propyl)-1H-benzo[d]imidazol-2(3H)-one as a purple oily foam (1.14 g, 2.96 mmol).

Workup

  1. washwashed with water
  2. dry with materialbrine and dried over anhydrous magnesium sulfate
  3. filtrationAfter filtration and concentration the crude product
  4. customwas chromatographed on silica gel eluting with 5-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b802698bd05f44729ba4db654879b481
Source dataset
uspto-grants-2014_03
Patent number
US08673897B2

Reaction notes

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