Ammonium iodide → HCID 58424316, compound

HRID 1408652Notes

Reaction equation

HRID 1408652 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][C:23]([Cl:26])=[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][CH:9]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[CH2:10]2)[N:12]=1

Participants

4

Reactant 2

HCID 25487Ammonium iodideHCID 58423987HCID 58423987, compound

Product 1

HCID 58424316HCID 58424316, compoundYield 12.4%

Reagents, catalysts & solvents 1

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

Procedure

A solution of 6-bromo-2-(4-chlorophenyl)-1′-methyl-2′-(methylthio)spiro[chroman-4,4′-imidazol]-5′(1′H)-one (300 mg, 0.67 mmol) and NH4I (194 mg, 1.33 mmol) in NH3/EtOH (5 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 2′-amino-6-bromo-2-(4-chlorophenyl)-1′-methylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (35 mg, 12%). 1H-NMR (MeOD): 2.19 (m, 1H), 2.41 (m, 1H), 3.11 (m, 3H), 5.15 (m, 0.5H), 5.38 (m, 0.5H), 6.78 (m, 1H), 6.82 (m, 0.5H), 7.02 (m, 0.5H), 7.23 (m, 1H), 7.31 (m, 3H), 7.44 (m, 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-62acdee2db8f47af901569b16ce3d46e
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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