Ammonium iodide → HCID 58423880, compound

HRID 2096377Notes

Reaction equation

HRID 2096377 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][O: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][O:22][CH2:21]3)[CH2:10]2)[N:12]=1

Participants

4

Reactant 3

HCID 25487Ammonium iodideHCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 58423900HCID 58423900, compound

Product 1

HCID 58423880HCID 58423880, compoundYield 107.9%

Procedure

A solution of 6-bromo-1′-methyl-2′-(methylthio)-2-(tetrahydro-2H-pyran-3-yl)spiro[chroman-4,4′-imidazol]-5′(1′H)-one (20 mg, 0.047 mmol), NH4I (54.5 mg, 0.37 mmol) in a solution of NH3/EtOH (2 mL, 8 N) was heated at 120° C. in a tube in a microwave reactor for 3 h. After cooling, the mixture was concentrated in vacuo to give 2′-amino-6-bromo-1′-methyl-2-(tetrahydro-2H-pyran-3-yl)spiro[chroman-4,4′-imidazol]-5′(1′H)-one (20 mg, 100%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-cddc47ab50f440e4a11c18ae55edc180
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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