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Imidazole → 5-Bromo-2-((triisopropylsilyloxy)methyl)thiazole

HRID 1487461
Notes
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Reaction equation

HRID 1487461 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH2:7][OH:8])=[N:4][CH:3]=1.N1C=CN=C1.CN(C)C=O.Cl[Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22]>C(OC(=O)C)C>[Br:1][C:2]1[S:6][C:5]([CH2:7][O:8][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])=[N:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 139400Triisopropylsilyl chlorideHCID 11953783(5-Bromo-1,3-thiazol-2-yl)methanol

Product 1

HCID 866954185-Bromo-2-((triisopropylsilyloxy)methyl)thiazoleYield 104%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Procedure

A 100 mL round bottom flask is charged with (5-bromothiazol-2-yl)methanol (2.5 g, 12.9 mmol), imidazole (1.75 g, 25.8 mmol), dimethylformamide (25 mL), and chlorotriisopropylsilane (3.4 mL, 15.5 mmol). The reaction is stirred at room temperature under nitrogen for 72 hours. Contents are diluted with ethylacetate (150 mL), washed with 0.5M hydrochloric acid (2×100 mL) and brine (100 mL), dried (Na2SO4), and concentrated under vacuum to afford the title compound (4.7 g): m/z (CI) M+H 350+352.

Workup

  1. washwashed with 0.5M hydrochloric acid (2×100 mL) and brine (100 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-63545f2e8b92429ebcfda3f92c7b25b8
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09428528B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes