Triethylamine → 3-[3-(4-Bromophenyl)-1,2,4-thiadiazol-5-yl]-4,4-dimethyl-1,3-oxazolidin-2-one

HRID 1436445Notes

Reaction equation

HRID 1436445 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([NH:13][C:14]([CH3:18])([CH3:17])[CH2:15][OH:16])[S:10][N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:27](Cl)([O:29]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[C:11]([N:13]3[C:14]([CH3:18])([CH3:17])[CH2:15][O:16][C:27]3=[O:29])[S:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 689033722-{[3-(4-Bromophenyl)-1,2,4-thiadiazol-5-yl]amino}-2-methylpropan-1-ol

Product 1

HCID 250273683-[3-(4-Bromophenyl)-1,2,4-thiadiazol-5-yl]-4,4-dimethyl-1,3-oxazolidin-2-oneYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2-{[3-(4-Bromophenyl)-1,2,4-thiadiazol-5-yl]amino}-2-methylpropan-1-ol (0.80 g, 2.4 mmol), prepared in the previous step, was dissolved in methylene chloride (20 mL), triethylamine (3.3 mL, 24 mmol) was added, and the mixture was cooled to 0° C. Triphosgene (1.8 g, 6.1 mmol) was added and the mixture was stirred for 2.5 h. The mixture was then diluted with methylene chloride and washed with 2N HCl, saturated NaHCO3, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (7.5% acetone/hexane) afforded the title compound (730 mg, 86%). Analytical HPLC: purity 100% at 210-370 nm, 11.0 min; 100% at 246 nm, 11.0 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

Workup

  1. washwashed with 2N HCl, saturated NaHCO3, brine
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-67352225eba440cc922695e0cafa9f4a
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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