Potassium Carbonate → HCID 58423942, compound

HRID 2096472Notes

Reaction equation

HRID 2096472 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:15](=O)[NH:14][C:13](=[S:17])[NH:12]3)[CH2:10][CH:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:8][C:5]2=[CH:6][CH:7]=1.Br[CH2:25][CH2:26][CH:27]1[CH2:29][CH2:28]1.[C:30]([O-:33])([O-])=O.[K+].[K+]>CC#N>[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:30](=[O:33])[N:14]([CH2:15][CH2:26][CH:27]4[CH2:29][CH2:28]4)[C:13]([S:17][CH2:25][CH2:26][CH:27]4[CH2:29][CH2:28]4)=[N:12]3)[CH2:10][CH:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:8][C:5]2=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22636989(2-Bromoethyl)cyclopropaneHCID 58423943HCID 58423943, compound

Product 1

HCID 58423942HCID 58423942, compoundYield 11.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-bromo-2-phenyl-2′-thioxospiro[chroman-4,4′-imidazolidin]-5′-one (250 mg, 0.644 mmol), excess (2-bromoethyl)cyclopropane (381 mg, 2.58 mmol), and solid K2CO3 (356 mg, 2.58 mmol) in CH3CN (10 mL) was stirred for 4 hours at 60° C. The mixture was filtered and the filtrate was concentrated. The crude product was purified by preparative TLC to give 6-bromo-1′-(2-cyclopropylethyl)-2′-(2-cyclopropylethylthio)-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (40 mg, 11%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-eebc1dfeb2ea4286a90a0ff5696ff218
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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