Ammonium iodide → HCID 58423991, compound

HRID 2096578Notes

Reaction equation

HRID 2096578 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[C:5]2([C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[O:10][CH:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:8]2)[N:4]=[C:3]1SC.[NH4+:25].[I-]>N.CCO>[NH2:25][C:3]1[N:2]([CH3:1])[C:6](=[O:7])[C:5]2([C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[O:10][CH:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:8]2)[N:4]=1

Participants

4

Reactant 2

HCID 25487Ammonium iodideHCID 58423793HCID 58423793, compound

Product 1

HCID 58423991HCID 58423991, compoundYield 11%

Reagents, catalysts & solvents 1

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

Procedure

A solution of 1′-methyl-2′-(methylthio)-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (50 mg, 0.148 mmol) and NH4I (42.9 mg, 0.296 mmol) in NH3/EtOH (4 mL, 1.5 N) is heated at 110° C. in a tube under microwave reactor for 2-2.5 h. After cooling, the mixture is concentrated in vacuo to give a residue, which is purified by preparative TLC to afford 2′-amino-1′-methyl-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (5 mg, 10%).

Workup

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

Sources & evidence

ORD record
ord-ea792687f9ed4474b7cdda1682a34899
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

Loading…