Sodium hydride → 3-(2,4-dibromo-1,3-thiazol-5-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazole

HRID 2282307Notes

Reaction equation

HRID 2282307 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:8]2[NH:12][CH:11]=[N:10][N:9]=2)=[C:5]([Br:7])[N:6]=1.[H-].[Na+].[CH3:15][Si:16]([CH2:19][CH2:20][O:21][CH2:22]Cl)([CH3:18])[CH3:17].CCOC(C)=O.CCCCCC>CN(C=O)C>[Br:1][C:2]1[S:3][C:4]([C:8]2[N:12]=[CH:11][N:10]([CH2:22][O:21][CH2:20][CH2:19][Si:16]([CH3:18])([CH3:17])[CH3:15])[N:9]=2)=[C:5]([Br:7])[N:6]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 21226206Ethyl acetate hexaneHCID 178419476HCID 178419476, compound

Product 1

HCID 580950363-(2,4-dibromo-1,3-thiazol-5-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazoleYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To the solution of 3-(2,4-dibromo-1,3-thiazol-5-yl)-4H-1,2,4-triazole (1.16 g, 3.74 mmol) in dry DMF (5.0 mL) at 0° C. was added portionwise sodium hydride (60%, 0.180 g, 4.49 mmol). The ice bath was removed, mixture was stirred for 5 min. at ambient temperature and cooled with ice bath. SEM chloride (0.795 mL, 4.49 mmol) in dry DMF (2.0 mL) was added dropwise and the mixture was stirred at room temperature for 2 hours. The mixture was quenched with ice-water, extracted with EtOAc, washed with brine, dried over Na2SO4, filtered, evaporated to give a crude oil. Chromatograph in a silica column using EtOAc/hexane (0/100 to 20/80) afforded white solid product (1.10 g, 67%). LCMS: (FA) ES+ 441. 1H NMR (400 MHz, d1-chloroform) 8.29 (s, 1H), 5.54 (s, 2H), 3.71 (t, J=8.28 Hz, 2H), 0.95 (t, J=8.28 Hz, 2H), 50.00 (s, 9H).

Workup

  1. customThe ice bath was removed
  2. temperaturecooled with ice bath
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. customThe mixture was quenched with ice-water
  5. extractionextracted with EtOAc
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customto give a crude oil

Sources & evidence

ORD record
ord-167a9798c9f64a0ba6f04a8209087a01
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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