Ammonium iodide → 2'-amino-1'-benzyl-2-bromo-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4'-imidazol]-5'(1'H)-one

HRID 590529

Reaction equation

[CH2:1]([N:8]1[C:12](=[O:13])[C:11]2([C:21]3[CH:20]=[C:19]([Br:22])[S:18][C:17]=3[CH2:16][CH2:15][CH2:14]2)[N:10]=[C:9]1SCC1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[NH4+:32]>N.CO>[NH2:32][C:9]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:12](=[O:13])[C:11]2([C:21]3[CH:20]=[C:19]([Br:22])[S:18][C:17]=3[CH2:16][CH2:15][CH2:14]2)[N:10]=1

Participants

Conditions

Temperature: 90 °C

Procedure

1′-Benzyl-2′-(benzylthio)-2-bromo-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4′-imidazol]-5′(1′H)-one (0.25 g, 0.5 mmol) and ammonium iodide (0.43 g, 3 mmol) were suspended in 7 N NH3/methanol solution (10 mL). The mixture was heated at 90° C. for 18 hr. The solution was concentrated in vacuo and the crude residue partitioned between water and dichloromethane. The product was extracted into dichloromethane (×3), the organic extracts were combined, dried (MgSO4) and concentrated in vacuo. The crude residue was purified on silica gel using 7 N NH3/methanol in dichloromethane (1:9) to afford the title compound as a foam (80 mg, 41%).

Workup

concentrationThe solution was concentrated in vacuo
customthe crude residue partitioned between water and dichloromethane
extractionThe product was extracted into dichloromethane (×3)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe crude residue was purified on silica gel using 7 N NH3/methanol in dichloromethane (1:9)

Sources & evidence

ORD record: ord-2488d9338b8c43bdb343adee1b9ce72c
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233982B2

Linked notes

Loading…