Potassium Carbonate → HCID 86711346, compound

HRID 926270Notes

Reaction equation

HRID 926270 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([CH:25]=[O:26])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S([CH2:37][N+:38]#[C-:39])(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CO.O>[C:1]([N:20]1[CH:24]=[C:23]([C:25]2[O:26][CH:39]=[N:38][CH:37]=2)[N:22]=[CH:21]1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehyde

Product 1

HCID 86711346HCID 86711346, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1-trityl-1H-imidazole-4-carbaldehyde (25.0 g, 73.9 mmol), TosMIC (14.42 g, 73.9 mmol) and K2CO3 (10.21 g, 73.9 mmol) in MeOH (750 mL) was heated to reflux for 3 h. The mixture was then allowed to cool to RT, diluted with H2O, and extracted with AcOEt. The combined org. layers were then washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (SiO2, heptane/AcOEt 100:0 to 0:100) gave the title compound (14.6 g). UPLC (2 min) rt 1.415 min.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. extractionextracted with AcOEt
  4. washlayers were then washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography (SiO2, heptane/AcOEt 100:0 to 0:100)

Sources & evidence

ORD record
ord-67dec7ad5cdc40c4bb74787a04a7c7f2
Source dataset
uspto-grants-2016_03
Patent number
US09284331B2

Reaction notes

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