Ammonium iodide → HCID 58423892, compound

HRID 2096473Notes

Reaction equation

HRID 2096473 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:15](=[O:16])[N:14]([CH2:17][CH2:18][CH:19]4[CH2:21][CH2:20]4)[C:13](SCCC4CC4)=[N:12]3)[CH2:10][CH:9]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[O:8][C:5]2=[CH:6][CH:7]=1.[NH4+:34].[I-].N.CCO>>[NH2:34][C:13]1[N:14]([CH2:17][CH2:18][CH:19]2[CH2:21][CH2:20]2)[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:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:10]2)[N:12]=1

Participants

4

Reactant 3

HCID 25487Ammonium iodideHCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 58423942HCID 58423942, compound

Product 1

HCID 58423892HCID 58423892, compoundYield 24%

Procedure

A solution of 6-bromo-1′-(2-cyclopropylethyl)-2′-(2-cyclopropylethylthio)-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (40 mg, 0.076 mmol), and NH4I (22 mg, 0.153 mmol) in a solution of NH3/EtOH (4 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-1′-(2-cyclopropylethyl)-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (8 mg, 24%). 1H-NMR (MeOD): 0.01 (m, 2H), 0.34 (m, 2H), 0.61 (m, 1H), 1.48 (m, 2H), 2.10 (m, 1H), 2.37 (m, 1H), 3.67 (m, 2H), 5.12 (d, 0.3H), 5.74 (d, 0.7H), 6.70 (m, 1H), 7.00 (m, 1H), 7.31 (m, 6H).

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-72271e0a3c264911ae23ffbe9e488c09
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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