Potassium Carbonate → HCID 22592129, compound

HRID 746648Notes

Reaction equation

HRID 746648 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][C:13]1[C:14]([S:22][CH3:23])=[N:15][C:16]([CH3:21])=[CH:17][C:18]=1[S:19][CH3:20])=[O:11].[CH3:24][O:25][C:26]([C:28]1[C:36]2[O:35][C:34]([SH:37])=[N:33][C:32]=2[CH:31]=[CH:30][CH:29]=1)=[O:27].C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>O.CN(C=O)C>[CH3:24][O:25][C:26]([C:28]1[C:36]2[O:35][C:34]([S:37][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][C:13]3[C:14]([S:22][CH3:23])=[N:15][C:16]([CH3:21])=[CH:17][C:18]=3[S:19][CH3:20])=[O:11])=[N:33][C:32]=2[CH:31]=[CH:30][CH:29]=1)=[O:27]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 22592164HCID 22592164, compoundHCID 178497587HCID 178497587, compound

Product 1

HCID 22592129HCID 22592129, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a DMF (4 ml) solution of 9-bromo-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]nonanamide (90 mg, 0.22 mmol) and 7-methoxycarbonyl-2-mercaptobenzoxazole (45 mg, 0.22 mmol) were added 18-crown-6 (6 mg, 0.02 mmol) and potassium carbonate (36 mg, 0.26 mmol), and the mixture was stirred at 80° C. for 4 hours. The reaction mixture was diluted with water, and then extracted with ethyl acetate. The organic layer was washed with water and then with a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. Subsequently, the solvent was distilled off, and the resulting crude product was recrystallized from a mixture of ethyl acetate and hexane to obtain 84 mg (yield 72%) of the desired compound as a colorless powdery crystal.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialwith a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
  4. distillationSubsequently, the solvent was distilled off
  5. customthe resulting crude product was recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-88de6a9a607245318b7bd60fd69cf446
Source dataset
uspto-grants-2008_07
Patent number
US07393866B2

Reaction notes

Loading…