1-(5-(Hydroxymethyl)-4-methylthiazol-2-yl)-3-(4-(trifluoromethyl)benzyl)imidazolidin-2-one → 4-Methyl-2-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiazole-5-carbaldehyde

HRID 2067638Notes

Reaction equation

HRID 2067638 reaction equation
[OH:1][CH2:2][C:3]1[S:7][C:6]([N:8]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[C:9]2=[O:24])=[N:5][C:4]=1[CH3:25]>ClCCl.C(OCC)(=O)C>[CH3:25][C:4]1[N:5]=[C:6]([N:8]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[C:9]2=[O:24])[S:7][C:3]=1[CH:2]=[O:1]

Participants

4

Reactant 1

HCID 250974421-(5-(Hydroxymethyl)-4-methylthiazol-2-yl)-3-(4-(trifluoromethyl)benzyl)imidazolidin-2-one

Product 1

HCID 580314234-Methyl-2-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiazole-5-carbaldehydeYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(5-(hydroxymethyl)-4-methylthiazol-2-yl)-3-(4-(trifluoromethyl)benzyl)imidazolidin-2-one (0.40 g, 1.07 mmol) in dichloromethane (50 mL) was added Dess-Mertin periodinane (0.60 g, 1.40 mmol). The reaction mixture was stirred for 6 hours at ambient temperature, and then diluted with ethyl acetate, washed with 10% sodium thiosulfate solution, saturated sodium bicarbonate solution and brine. The organic solution was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to afford the title compound in 80% yield (0.32 g): MS (ES+) m/z 370.1 (M+1).

Workup

  1. washwashed with 10% sodium thiosulfate solution, saturated sodium bicarbonate solution and brine
  2. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1626b8e779a54f469678ea8273d8e417
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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