Ammonium iodide → HCID 58424384, compound

HRID 1408570Notes

Reaction equation

HRID 1408570 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][CH:9]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[O:8][C:5]2=[CH:6][CH:7]=1.[NH4+:26].[I-]>N.CCO>[NH2:26][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][CH:9]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:10]2)[N:12]=1

Participants

4

Reactant 2

HCID 25487Ammonium iodideHCID 58423929HCID 58423929, compound

Product 1

HCID 58424384HCID 58424384, compoundYield 57.4%

Reagents, catalysts & solvents 1

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

Procedure

A solution of 6-bromo-2-cyclohexyl-1′-methyl-2′-(methylthio)spiro[chroman-4,4′-imidazol]-5′(1′H)-one (170 mg, 0.40 mmol), NH4I (117 mg, 0.80 mmol) in a solution of NH3/EtOH (10 mL, 1.5 N) was heated at 120° C. in a 40 mL test tube under microwave reactor for 3 hrs. After cooling, the mixture was concentrated in vacuo to give the residue, which was purified by preparative TLC to afford 2′-amino-6-bromo-2-cyclohexy-1′-methylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (90 mg, 57%).

Workup

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

Sources & evidence

ORD record
ord-7ccc3397c4b145df836834b07e55ed58
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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