Diisopropylethylamine → 3-[4-(4-Bromophenyl)-5-methyl-1,3-thiazol-2-yl]-4,4-dimethyl-1,3-oxazolidin-2-one

HRID 1436385Notes

Reaction equation

HRID 1436385 reaction equation
C(N(C(C)C)CC)(C)C.Br.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:19]=[C:20]([NH:24][C:25]([CH3:29])([CH3:28])[CH2:26][OH:27])[S:21][C:22]=2[CH3:23])=[CH:14][CH:13]=1.Cl[C:31](Cl)([O:33]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[N:19]=[C:20]([N:24]3[C:25]([CH3:29])([CH3:28])[CH2:26][O:27][C:31]3=[O:33])[S:21][C:22]=2[CH3:23])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 866185872-{[4-(4-Bromophenyl)-5-methyl-1,3-thiazol-2-yl]amino}-2-methylpropan-1-ol hydrobromide

Product 1

HCID 688609823-[4-(4-Bromophenyl)-5-methyl-1,3-thiazol-2-yl]-4,4-dimethyl-1,3-oxazolidin-2-oneYield 1,270.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diisopropylethylamine (10.0 mL, 57.4 mmol) was added under nitrogen to a mixture of 2-{[4-(4-bromophenyl)-5-methyl-1,3-thiazol-2-yl]amino}-2-methylpropan-1-ol hydrobromide (5.2 g, 1.2 mmol), prepared in the previous step, and 120 mL of methylene chloride at room temperature. A white solid formed. The mixture was cooled to ice bath temperature and triphosgene (5.2 g, 1.8 mmol) in 60 mL of methylene chloride was added dropwise over approximately 2 h. After the addition, the reaction became homogeneous. The reaction was stirred at ice bath temperature for approximately 2 h and then at room temperature overnight. The reaction was extracted with aqueous sodium hydroxide and the solvent removed under reduced pressure to give 5.6 g of a solid. Purification of the solid on a Horizon™ Flash Collector (the Biotage FLASH 25+™ cartridge) using a linear gradient of 36% methylene chloride in hexane to 75% methylene chloride in hexane gave the title compound (2.77 g, 63%) as a white solid, mp 175-176.5° C.; MS (ESI) m/z 367 [M+H]+. Anal. Calcd for C15H15BrN2O2S: C, 49.06; H, 4.12; N, 7.63. Found: C, 48.94; H, 4.19; N, 7.56.

Workup

  1. customA white solid formed
  2. additionwas added dropwise over approximately 2 h
  3. additionAfter the addition
  4. customat room temperature
  5. customovernight
  6. extractionThe reaction was extracted with aqueous sodium hydroxide
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-cc48de7fca524ab7a10babaaf664eeb2
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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