Lithium hydroxide, monohydrate → HCID 59481298, compound

HRID 560592Notes

Reaction equation

HRID 560592 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-ad0f2ef86568459cb85ebc5721e430b9
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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