Ammonium iodide → HCID 58423949, compound

HRID 2096431Notes

Reaction equation

HRID 2096431 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:15](=[O:16])[N:14]([CH3:17])[C:13](SC)=[N:12]3)[CH2:10][C:9]([CH3:26])([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:8][C:5]2=[CH:6][CH:7]=1.[NH4+:27].[I-]>N.CCO>[NH2:27][C:13]1[N:14]([CH3:17])[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:9]([CH3:26])([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:10]2)[N:12]=1

Participants

4

Reactant 2

HCID 25487Ammonium iodideHCID 58424217HCID 58424217, compound

Product 1

HCID 58423949HCID 58423949, compoundYield 18%

Reagents, catalysts & solvents 1

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

Procedure

A solution of 6-bromo-1′,2-dimethyl-2′-(methylthio)-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (292 mg, 0.667 mmol), NH4I (245.7 mg, 1.668 mmol) in a solution of NH3/EtOH (30 mL, 5 N) was heated at 110° C. in a CEM tube in a microwave reactor for 4 h. After cooling, the mixture was concentrated in vacuum to give the residue, which was purified by preparative TLC to afford 2′-amino-6-bromo-1′,2-dimethyl-2-phenylspiro [chroman-4,4′-imidazol]-5′(1′H)-one (45 mg, 18%). 1H-NMR (MeOD): 1.63 (s, 3H), 1.77 (s, 3H), 2.74 (d, 2H), 6.75 (d, 1H), 7.06 (d, 1H), 7.22 (m, 1H), 7.31 (m, 3H), 7.45 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-d7cd7e50997148d0b472175f51b97c71
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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