Chloroform → HCID 59526358, compound

HRID 385743Notes

Reaction equation

HRID 385743 reaction equation
CC([O-])(C)C.[K+].[N+:7]([C:10]1[S:14][C:13]([C:15]2[N:19]=[CH:18][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[N:16]=2)=[CH:12][CH:11]=1)([O-:9])=[O:8].[CH:28](Cl)([Cl:30])[Cl:29]>C1COCC1.CN(C=O)C>[Cl:29][CH:28]([Cl:30])[C:11]1[CH:12]=[C:13]([C:15]2[N:19]=[CH:18][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[N:16]=2)[S:14][C:10]=1[N+:7]([O-:9])=[O:8]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 23665647Potassium tert-butoxideHCID 59526171HCID 59526171, compound

Product 1

HCID 59526358HCID 59526358, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of t-BuOK (9.07 g, 81 mmol) in THF (50 mL) was cooled to −78° C. before adding DMF (70 mL). A solution of 3-(5-nitro-2-thienyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazole (6.60 g, 20.22 mmol) and CHCl3 (1.79 mL, 22.24 mmol) in DMF (35 mL) was added dropwise over 1 h. After complete addition, the reaction was stirred at −78° C. for 30 min, quenched with 2 N HCl, allowed to warm to room temperature, and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Purification of the crude residue by flash chromatography (0-25% EtOAc/hexanes) afforded the title compound as a yellow solid.

Workup

  1. additionAfter complete addition
  2. customquenched with 2 N HCl
  3. temperatureto warm to room temperature
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customPurification of the crude residue by flash chromatography (0-25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-27714d8fac4b4a2e839ba8c1dd66f20f
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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