Triethylamine → 1-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]imidazolidin-2-one

HRID 1993741Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([NH:13][CH2:14][CH2:15][NH2:16])[S:11][CH:12]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:25](Cl)([O:27]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([N:13]3[CH2:14][CH2:15][NH:16][C:25]3=[O:27])[S:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]ethane-1,2-diamine (1.1 g, 3.7 mmol), prepared in the previous step, was dissolved in 30 mL methylene chloride and triethylamine (5.1 mL, 36.9 mmol) was added. The mixture was cooled to 0° C., triphosgene (2.7 g, 9.2 mmol) was added, and the mixture was stirred for 3 h. The mixture was diluted with ethyl acetate, washed with NaHCO3, water, brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Flash chromatography (2% methanol/methylene chloride) afforded the title compound (250 mg, 21%) as a white solid; mp 230-233° C. HRMS: calcd for C12H10BrN3OS+H+, 323.98007; found (ESI, [M+H]+), 323.9808. Analytical HPLC: retention time 9.7 min, 210-370 nm the Xterra® RP18 column, 3.5μ, 150×4.6 mm 40 C 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min, 1.2 mL/min 5 μL injection.

Workup

washwashed with NaHCO3, water, brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-62d33554c9cb48db9f3107aa00b2f794
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652018B2

Reaction notes

Loading…