Ammonium iodide → HCID 58424333, compound

HRID 2096402Notes

Reaction equation

HRID 2096402 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]=[C:22]([F:26])[C:21]=3[F:27])[O:8][C:5]2=[CH:6][CH:7]=1.[NH4+:28].[I-].N.CCO>>[NH2:28][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]=[C:22]([F:26])[C:21]=3[F:27])[CH2:10]2)[N:12]=1

Participants

4

Reactant 3

HCID 25487Ammonium iodideHCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 58423912HCID 58423912, compound

Product 1

HCID 58424333HCID 58424333, compoundYield 60%

Procedure

A solution of 6-bromo-2-(2,3-difluorophenyl)-1′-methyl-2′-(methylthio) spiro[chroman-4,4′-imidazol]-5′(1′H)-one (63 mg, 0.14 mmol), NH4I (60.6 mg, 0.42 mmol) in a solution of NH3/EtOH (3 mL, 1.5 N) was heated at 110° C. in a 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-(2,3-difluorophenyl)-1′-methylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (35 mg, 60%). 1H-NMR (CDCl3): 2.31 (d, 1H), 2.45 (t, 1H), 3.27 (s, 3H), 6.12 (d, 1H), 6.87 (m, 1H), 7.09 (m, 3H), 7.34 (m, 2H), 7.45 (m, 1H).

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-ad688322972242db8577ad12b362ad5d
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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