Lithium hydroxide, monohydrate → HCID 59481298, compound

HRID 2067365Notes

Reaction equation

HRID 2067365 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:13]2=[O:23])[S:5][C:6]=1[C:7]([O:9]CC)=[O:8].O.[OH-].[Li+]>O1CCCC1.CO.O>[CH3:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:16][CH2:15][N:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:13]2=[O:23])[S:5][C:6]=1[C:7]([OH:9])=[O:8]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58031446Ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 59481298HCID 59481298, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylate (1.49 g, 4.49 mmol) in tetrahydrofuran (30 mL), methanol (10 mL) and water (10 mL) was added lithium hydroxide monohydrate (0.38 g, 9.00 mmol) at ambient temperature. The resulting reaction mixture was heated to reflux for 14 hours. The solvent was removed in vacuo, and the residue was neutralized to pH 4˜5 with 10% hydrochloric acid. The resulting precipitate was filtered and dried to afford the title compound in 93% yield (1.27 g): mp 286-289° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.88-7.34 (m, 5H), 4.10-3.76 (m, 4H), 2.49 (s, 3H); MS (ES+) m/z 304.3 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 14 hours
  4. customThe solvent was removed in vacuo
  5. filtrationThe resulting precipitate was filtered
  6. customdried

Sources & evidence

ORD record
ord-0549c82f77b5459182855b36cc37ed26
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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