Acetonitrile → HCID 21890139, compound

HRID 721482Notes

Reaction equation

HRID 721482 reaction equation
C(#N)C.[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[N:12]=[CH:11][CH:10]=[C:9]2[O:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[O:27])=[CH:21][CH:20]=1.[CH3:35][C:36]1[CH:43]=[CH:42][CH:41]=[CH:40][C:37]=1[CH2:38]Br.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[N:12]=[CH:11][CH:10]=[C:9]2[O:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][CH:29]2[CH2:34][CH2:33][N:32]([CH2:35][C:36]3[CH:43]=[CH:42][CH:41]=[CH:40][C:37]=3[CH3:38])[CH2:31][CH2:30]2)=[O:27])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6992o-Xylyl bromideHCID 11430Potassium CarbonateHCID 21890637HCID 21890637, compound

Product 1

HCID 21890139HCID 21890139, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetonitrile (10 ml) was added to the compound (1) (139 mg), 2-methylbenzyl bromide (0.03 ml), and potassium carbonate (81 mg), and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with chloroform. The extract was washed with saturated brine and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin-layer chromatography using chloroform/methanol for development. Diethyl ether was added to the purification product, and the precipitated crystal was collected by filtration and was washed to give the title compound (46 mg, yield 45%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe extract was washed with saturated brine
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customThe residue was purified by thin-layer chromatography
  6. additionDiethyl ether was added to the purification product
  7. filtrationthe precipitated crystal was collected by filtration
  8. washwas washed

Sources & evidence

ORD record
ord-11763085a1fe449a9a61e85d3aa1e0ec
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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