Ammonium iodide → HCID 58423834, compound

HRID 2096470Notes

Reaction equation

HRID 2096470 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C@:11]3([C:15](=[O:16])[N:14]([CH2:17][CH2:18][CH3:19])[C:13](SCCC)=[N:12]3)[CH2:10][C@H:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:8][C:5]2=[CH:6][CH:7]=1.[NH4+:30].[I-]>N.CCO>[NH2:30][C:13]1[N:14]([CH2:17][CH2:18][CH3:19])[C:15](=[O:16])[C@:11]2([C:4]3[C:5](=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=3)[O:8][C@@H:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:10]2)[N:12]=1

Participants

4

Reactant 2

HCID 25487Ammonium iodideHCID 58424053HCID 58424053, compound

Product 1

HCID 58423834HCID 58423834, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 22020343Ethanol, reaction products with ammonia, distn. residuesSolvent

Procedure

A solution of (2R,4S)-6-bromo-2-phenyl-1′-propyl-2′-(propylthio)spiro[chroman-4,4′-imidazol]-5′(1′H)-one (75 mg, 0.16 mmol), and NH4I (46 mg, 0.32 mmol) in NH3/EtOH (4 mL, 1.5 N) was heated at 110° C. in a tube in a microwave reactor for 2-2.5 h. After cooling, the mixture was concentrated in vacuo to give a residue, which was purified by preparative TLC to afford (2R,4S)-2′-amino-6-bromo-2-phenyl-1′-propylspiro-[chroman-4,4′-imidazol]-5′(1′H)-one (15 mg, 23%). 1H-NMR (MeOD): 1.00 (m, 3H), 1.45 (m, 2H), 2.23 (m, 1H), 2.48 (m, 1H), 3.75 (m, 2H), 5.85 (m, 1H), 6.90 (m, 1H), 7.14 (m, 1H), 7.40 (m, 6H).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. customto give a residue, which
  4. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-7d173790707b44a7952b77cf39298b57
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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