Ammonium iodide → HCID 58424032, compound

HRID 1408580Notes

Reaction equation

HRID 1408580 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]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[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][CH:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[CH2:10]2)[N:12]=1

Participants

4

Reactant 3

HCID 25487Ammonium iodideHCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 58423765HCID 58423765, compound

Product 1

HCID 58424032HCID 58424032, compoundYield 70.3%

Procedure

A solution of 6-bromo-2-(2-fluorophenyl)-1′-methyl-2′-(methylthio)spiro[chroman-4,4′-imidazol]-5′(1′H)-one (80 mg, 0.183 mmol) and NH4I (53.21 mg, 0.367 mmol) in a solution of NH3/EtOH (2 mL, 1.5 N) was heated at 110° C. in a tube under microwave reactor for 3 h. After cooling, the mixture was concentrated in vacuo to give a residue, which was purified by preparative TLC to afford 2′-amino-6-bromo-2-(2-fluorophenyl)-1′-methylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (52 mg, 70%). 1H-NMR (MeOD): 2.15 (d, 1H), 2.25 (d, 1H), 3.20 (s, 3H), 6.15 (d, 1H), 6.78 (d, 1H), 6.99 (t, 1H), 7.05 (s, 1H), 7.15 (t, 1H), 7.25 (d, 2H), 7.50 (t, 1H).

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-31695980ef244cd7aee28a721a1080ea
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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