Imidazole → HCID 11099363, compound

HRID 1779704Notes

Reaction equation

HRID 1779704 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:9][N:10]([CH3:23])[C:11]([C:13]1[CH:21]=[CH:20][C:16]2[O:17][CH2:18][O:19][C:15]=2[C:14]=1[OH:22])=[O:12].N1C=CN=C1>C(Cl)Cl>[CH3:9][N:10]([CH3:23])[C:11]([C:13]1[CH:21]=[CH:20][C:16]2[O:17][CH2:18][O:19][C:15]=2[C:14]=1[O:22][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[O:12]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 19956534HCID 19956534, compound

Product 1

HCID 11099363HCID 11099363, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

t-Butyldimethylsilyl chloride (4.02 g, 26.67 mmol) in CH2Cl2 (25 ml) was added to a solution of N,N-dimethyl-4-hydroxy-1,3-benzodioxole-5-carboxamide (5) (4.49 g, 20.5 mmol) and imidazole (3.63 g, 53.3 mmol) in CH2Cl2 (25 ml). The solution was stirred for 3 h at rt, during which time a white solid precipitated. The mixture was washed with brine, dried over MgSO4 and concentrated. Chromatography on silica (hexane/ethyl acetate, 1:1) afforded 9 (5.44 g, 82%) as a crystalline solid. 1H NMR (270 MHz, CDCl3) ε 6.75 (d, J=8.0 Hz, 1H), 6.50 (d, J=8.0 Hz, 1H), 5.92 (s, 2H), 3.03 (s, 3H), 2.87 (s, 3H), 0.94 (s, 9H), 0.16 (bs, 6H). 13C NMR (100 MHz, CDCl3) ε 168.9 (C), 149.3 (C), 137.0 (C), 135.5 (C), 124.9 (C), 121.4 (CH), 102.8 (CH), 101.0 (CH2), 38.2 (CH3), 34.9 (CH3), 25.4 (3CH3), 18.1 (C), -4.6 (2CH3).

Workup

  1. customprecipitated
  2. washThe mixture was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-04f11e19472d4389b20d29bd21161349
Source dataset
uspto-grants-1997_05
Patent number
US05627280

Reaction notes

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