Triethylamine → HCID 22257870, compound

HRID 1610795Notes

Reaction equation

HRID 1610795 reaction equation
C(N(CC)CC)C.[Si:8](Cl)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].[OH:16][CH2:17][C:18]1[NH:19][C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=1>>[Si:8]([O:16][CH2:17][C:18]1[NH:22][C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[N:19]=1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 785692-(Hydroxymethyl)-1H-benzimidazole

Product 1

HCID 22257870HCID 22257870, compoundYield 97%

Procedure

At room temperature, triethylamine (2.27 ml, 16.3 mmol) and TBDMS chloride (1.65 g, 10.95 mmol) were added to a solution of 2-hydroxymethylbenzimidazole (1.48 g, 9.95 mmol) in DMF-(30 ml). After 3.5 h, the reaction-was terminated by addition of water, the mixture was extracted with diethyl ether and the organic phase was dried over sodium sulphate. Chromatography (silica gel, cyclohexane:ethyl acetate 2:1, Rf=0.35) gave 2.52 g of 2-tert-butyldimethylsilyloxymethyl-benzimidazole (97% of theory) as a brownish powder. MS (DCI, NH3)=263 (M+H+). 1H-NMR (DMSO-d6): 0.00 (6H, s); 0.80 (9H, s); 4.75 (2H, s); 7.0-7.1 (2H, m); 7.4-7.5 (2H, m); 12.15 (1H, br s).

Workup

  1. customthe reaction-was terminated by addition of water
  2. extractionthe mixture was extracted with diethyl ether
  3. dry with materialthe organic phase was dried over sodium sulphate

Sources & evidence

ORD record
ord-7bbce70ad00140ac8112801eeb27961a
Source dataset
uspto-grants-2006_01
Patent number
US06984642B1

Reaction notes

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