Acetonitrile → HCID 58424179, compound

HRID 1408656Notes

Reaction equation

HRID 1408656 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:15](=[O:16])[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.[C:24]([O-])([O-])=O.[K+].[K+].[CH2:30](Br)[CH2:31][CH3:32].[CH3:34][C:35]#N>>[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:15](=[O:16])[N:14]([CH2:30][CH2:31][CH3:32])[C:13]([S:17][CH2:24][CH2:35][CH3:34])=[N:12]3)[CH2:10][CH:9]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[O:8][C:5]2=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 58423943HCID 58423943, compound

Product 1

HCID 58424179HCID 58424179, compoundYield 90%

Procedure

To a mixture of 6-bromo-2-phenyl-2′-thioxospiro[chroman-4,4′-imidazolidin]-5′-one (300 mg, 0.77 mmol) and K2CO3 (427 mg, 3.1 mmol) in CH3CN (6 mL) was added PrBr (380 mg, 3.1 mmol). The reaction mixture was refluxed for 2 h. The mixture was filtered, and the filtrate was concentrated to give a residue, which was purified by preparative TLC to give 6-bromo-2-phenyl-1′-propyl-2′-(propylthio)spiro[chroman-4,4′-imidazol]-5′(1′H)-one (285 mg, 90%). 1H-NMR (CDCl3): 0.87 (m, 3H), 1.00 (m, 3H), 1.64 (m, 2H), 1.73 (m, 2H), 1.89 (m, 1H), 2.48 (m, 1H), 3.16 (m, 2H), 3.44 (m, 2H), 5.82 (m, 1H), 6.81 (m, 2H), 7.22 (m, 1H), 7.30 (m, 3H), 7.48 (m, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customto give a residue, which
  5. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-9108d5e5e7cc44cc850ba7d328b31045
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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