Triethylamine → 1-(5-Acetyl-4-methylthiazol-2-yl)imidazolidin-2-one

HRID 1882400Notes

Reaction equation

HRID 1882400 reaction equation
[C:1]([C:4]1[S:8][C:7]([NH2:9])=[N:6][C:5]=1[CH3:10])(=[O:3])[CH3:2].C(N(CC)CC)C.Cl[CH2:19][CH2:20][N:21]=[C:22]=[O:23]>O1CCCC1>[C:1]([C:4]1[S:8][C:7]([N:9]2[CH2:19][CH2:20][NH:21][C:22]2=[O:23])=[N:6][C:5]=1[CH3:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 160352-Chloroethyl isocyanateHCID 7208825-Acetyl-2-amino-4-methylthiazole

Product 1

HCID 579197381-(5-Acetyl-4-methylthiazol-2-yl)imidazolidin-2-oneYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-acetyl-2-amino-4-methylthiazole (5.50 g, 35.20 mmol) in tetrahydrofuran (200 mL) was added triethylamine (15.0 mL, 107.6 mmol) and 2-chloroethyl isocyanate (3.90 mL, 45.70 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, and then heated to reflux for 27 hours. The solvent was removed in vacuo, and the residue was washed with water (200 mL) and ethyl acetate/hexanes (1/1, 50 mL) to afford the title compound in 99% yield (7.9 g): MS (ES+) m/z 226.1 (M+1).

Workup

  1. temperatureheated
  2. temperatureto reflux for 27 hours
  3. customThe solvent was removed in vacuo
  4. washthe residue was washed with water (200 mL) and ethyl acetate/hexanes (1/1, 50 mL)

Sources & evidence

ORD record
ord-92fec1676d7a4109bdecc0b34c5abd35
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

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