Hydrochloric Acid → HCID 58550529, compound

HRID 1891006Notes

Reaction equation

HRID 1891006 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH2:14][CH:15]1[CH2:19][CH2:18][CH2:17][O:16]1)C.[NH2:22][C:23]([NH2:25])=[S:24].C([O-])([O-])=O.[K+].[K+].Cl>COCCO.O>[O:16]1[CH2:17][CH2:18][CH2:19][CH:15]1[CH2:14][O:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:6]1[NH:25][C:23](=[S:24])[NH:22][C:4](=[O:3])[CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2723790ThioureaHCID 58550541HCID 58550541, compound

Product 1

HCID 58550529HCID 58550529, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent

Procedure

To a solution of 3-oxo-3-[2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-propionic acid ethyl ester (0.9 g, 3.08 mmol) in 2-methoxyethanol (5 mL) was added thiourea (0.31 g, 4.08 mmol) and K2CO3 (0.56 g, 4 mmol). The reaction mixture refluxed 5-6 h. After cooling, a mixture poured into water (10 mL), adjusted to pH 3 with 10% HCl and extracted with ethyl acetate (2×10 mL). Organic layers were combined, washed with water (10 mL), then dried over anhydrous sodium sulfate, concentrated and triturated with diethyl ether to obtained 0.6 g (64%) 6-[2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one as a beige solid.

Workup

  1. temperatureThe reaction mixture refluxed 5-6 h
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate (2×10 mL)
  4. washwashed with water (10 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-f9118802febf49c0a0c9375221972020
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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