Imidazole → HCID 178455393, compound

HRID 1421431Notes

Reaction equation

HRID 1421431 reaction equation
[CH2:1]([N:8]([CH2:16][C@H:17]([OH:28])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[C:21]=1[NH2:27])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=[CH:30]1.[Si:34](Cl)([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35]>CN(C)C=O>[CH3:35][Si:34]([CH3:36])([C:37]([CH3:40])([CH3:39])[CH3:38])[O:28][C@@H:17]([CH2:16][N:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:18][O:19][C:20]1[C:21]2[NH:27][CH:30]=[N:26][C:22]=2[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 54261304(2S)-1-(2,3-Diaminophenoxy)-3-(dibenzylamino)propan-2-ol

Product 1

HCID 178455393HCID 178455393, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-[3-(N,N-Dibenzylamino)-2-hydroxypropoxy]-2,3-diaminobenzene (1 g, 2.7 mmol) was dissolved in N,N Dimethylformamide (10 mL) and imidazole (0.27 g, 4.0 mmol) and tert-butyldimethylsilyl chloride (0.6 g, 4.0 mmol) were added. The solution was stirred at ambient temperature for 18 hours and then was partitioned between chloroform and water. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo to give the desired benzimidazole 1.3 g (96%). NMR.

Workup

  1. customwas partitioned between chloroform and water
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-197915e13a5f4b5d8fdb803cd9752555
Source dataset
uspto-grants-2000_06
Patent number
US06075040

Reaction notes

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