Ammonia → HCID 118033080, compound

HRID 590524

Reaction equation

HRID 590524 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[C:5]2([C:15]3[CH:14]=[CH:13][S:12][C:11]=3[CH2:10][CH2:9][CH2:8]2)[N:4]=[C:3]1SC.[I-].[NH4+:19].N>CO>[NH2:19][C:3]1[N:2]([CH3:1])[C:6](=[O:7])[C:5]2([C:15]3[CH:14]=[CH:13][S:12][C:11]=3[CH2:10][CH2:9][CH2:8]2)[N:4]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25487Ammonium iodideHCID 1180330781'-Methyl-2'-(methylthio)-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4'-imidazol]-5'(1'H)-one

Product 1

HCID 118033080HCID 118033080, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1′-Methyl-2′-(methylthio)-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4′-imidazol]-5′(1′H)-one (1.5 g, 5.63 mmol), ammonium iodide (4.89 g, 33.78 mmol) and 7 N ammonia in methanol (20 mL) were heated at 90° C. for 12 h. The solvent was then evaporated under reduced pressure and the residue was partitioned between water and dichloromethane. The dichloromethane extracts were combined, dried over magnesium sulphate and evaporated under reduced pressure to give an oil. This consisted of the title compound as the major component and its minor regioisomer in a 2:1 ratio. The oil was loaded onto a Biotage SNAP cartridge and eluted with dichloromethane-dichloromethane/7N ammonia in methanol (9:1). The appropriate fractions were combined and evaporated under reduced pressure to give 2′-amino-1′-methyl-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4′-imidazol]-5′(1′H)-one as a foam (800 mg, 60%).

Workup

  1. customThe solvent was then evaporated under reduced pressure
  2. customthe residue was partitioned between water and dichloromethane
  3. dry with materialdried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customto give an oil

Sources & evidence

ORD record
ord-8272d6434bfd4a528cc703711973edfa
Source dataset
uspto-grants-2016_01
Patent number
US09233982B2

Linked notes

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