Triethylamine → HCID 22257870, compound

HRID 2083984Notes

Reaction equation

HRID 2083984 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>CN(C=O)C>[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

5

Reactant 3

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

Product 1

HCID 22257870HCID 22257870, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At room temperature, triethylamine (2.27 ml, 163 mmol) and TBDMS chloride (1.65 g, 10.95 mmol) were added to a solution of 2-hydroxymethylbenzimidazole (1.4 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-butyldimethylsilyloxymethylbenzimidazole (97% of theory) as a brownish powder. MS (DCl, 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-52790773dd8540fda988de1f8b02b0e9
Source dataset
uspto-grants-2004_04
Patent number
US06716849B1

Reaction notes

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