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Potassium Carbonate → 1-(4-Methyl-5-(oxazol-5-yl)thiazol-2-yl)-3-(4-(trifluoromethyl)benzyl)-imidazolidin-2-one

HRID 2067639
Notes
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Reaction equation

HRID 2067639 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:9]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[C:10]2=[O:25])[S:5][C:6]=1[CH:7]=[O:8].C(=O)([O-])[O-].[K+].[K+].S([CH2:42][N+:43]#[C-:44])(C1C=CC(C)=CC=1)(=O)=O>CO.C(OCC)(=O)C>[CH3:1][C:2]1[N:3]=[C:4]([N:9]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[C:10]2=[O:25])[S:5][C:6]=1[C:7]1[O:8][CH:44]=[N:43][CH:42]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 580314234-Methyl-2-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiazole-5-carbaldehyde

Product 1

HCID 580316541-(4-Methyl-5-(oxazol-5-yl)thiazol-2-yl)-3-(4-(trifluoromethyl)benzyl)-imidazolidin-2-oneYield 47%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-methyl-2-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiazole-5-carbaldehyde (0.32 g, 0.86 mmol) in methanol (20 mL) was added potassium carbonate (0.30 g, 2.17 mmol) and tosylmethyl isocyanide (0.23 g, 1.17 mmol). The reaction mixture was stirred at ambient temperature for 1 h, heated to reflux for 1 h, and then cooled to ambient temperature. The mixture was diluted with ethyl acetate, washed with water and brine. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to afford the title compound as a colorless solid in 47% yield (0.32 g): mp 160-162° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.85 (s, 1H), 7.59 (d, J=8.1 Hz, 2H), 7.40 (d, J=8.1 Hz, 2H), 7.07 (s, 1H), 4.53 (s, 2H), 4.12-4.06 (m, 2H), 3.49-3.44 (m, 2H), 2.43 (s, 3H); 1H NMR (75 MHz, CDCl3) δ 157.5, 155.6, 149.8, 145.4, 145.1, 139.8, 130.5, 128.5, 125.9, 122.4, 122.1, 111.7, 47.6, 42.1, 42.0, 16.7; MS (ES+) m/z 409.1 (M+1).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. temperaturecooled to ambient temperature
  4. washwashed with water and brine
  5. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a9ef7e88aae141d1922c3aea8db74fb7
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08293768B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes