Imidazole → HCID 178455393, compound

HRID 1957498Notes

Reaction equation

HRID 1957498 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 (1g, 2.7mmol) was dissolved in N,N Dimethylformamide (10 mL) and imidazole (0.27g, 4.0 mmol) and tert-butyldimethylsilyl chloride (0.6g, 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 1.3g (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-7689a6e9e7f44f9b8cc50102f028cce5
Source dataset
uspto-grants-1998_07
Patent number
US05786356

Reaction notes

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