Sodium Hydroxide → 3-[2-(4-Amino-phenyl)-2-oxo-ethyl]-2-methyl-5-phenyl-5-propyl-3,5-dihydro-imidazol-4-one

HRID 507405Notes

Reaction equation

[CH3:1][C:2]1[N:6]([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)=[O:9])[C:5](=[O:19])[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([CH2:20][CH2:21][CH3:22])[N:3]=1.O.O.Cl[Sn]Cl.[OH-].[Na+]>C(O)C>[NH2:16][C:13]1[CH:12]=[CH:11][C:10]([C:8](=[O:9])[CH2:7][N:6]2[C:5](=[O:19])[C:4]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([CH2:20][CH2:21][CH3:22])[N:3]=[C:2]2[CH3:1])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of (+/−)-2-methyl-3-[2-(4-nitro-phenyl)-2-oxo-ethyl]-5-phenyl-5-propyl-3,5-dihydro-imidazol-4-one (528 mg, 1.4 mmol) and SnCl2.2H2O (1.92 g, 8.4 mmol) in 15 mL ethanol is heated to 80° C. for 2 hours. The reaction mixture is poured on to 1M sodium hydroxide solution and extracted with ethyl acetate. The combined organic phases are tried and evaporated to yield (+/−)-3-[2-(4-amino-phenyl)-2-oxo-ethyl]-2-methyl-5-phenyl-5-propyl-3,5-dihydro-imidazol-4-one (475 mg, 97%). LCIMS at 254 nm; [M+H] 350; Rt 2.506 min.

Workup

extractionextracted with ethyl acetate
customevaporated

Sources & evidence

ORD record: ord-6c5609c2ba3f463fa0d5d001c4028693
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786155B2

Reaction notes

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