Hydrochloric Acid → HCID 178489621, compound

HRID 1599036Notes

Reaction equation

HRID 1599036 reaction equation
C([O:3][C:4](=O)[CH:5]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])[C:6](OCC)=[O:7])C.[NH2:21][C:22]([NH2:24])=[S:23].[CH3:25][O-].[Na+].Cl>CO>[OH:3][C:4]1[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])=[C:6]([OH:7])[N:24]=[C:22]([S:23][CH3:25])[N:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2723790ThioureaHCID 10942334Sodium MethoxideHCID 11140560Diethyl (2-methoxyphenoxy)propanedioate

Product 1

HCID 178489621HCID 178489621, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (2-methoxyphenoxy)malonic acid diethyl ester (10.0 g) and thiourea (4.04 g) in methanol (100 ml) is added dropwise with stirring a 28% solution of sodium methoxide in methanol (17.07 g) over a period of 30 minutes under ice-cooling. The mixture is stirred at room temperature overnight. After the reaction is completed, the mixture is evaporated under reduced pressure to remove the solvent, and water (200 ml) is added to the residue. To the mixture is further added methyl iodide (3.30 ml), and the mixture is reacted at room temperature for three hours. The reaction solution is acidified with 10% aqueous hydrochloric acid, and the precipitated crystals are collected by filtration, washed with water, and dried to give 4,6-dihydroxy-5-(2-methoxyphenoxy)-2-methylthiopyrimidine (8.90 g).

Workup

  1. temperaturecooling
  2. customthe mixture is evaporated under reduced pressure
  3. customto remove the solvent, and water (200 ml)
  4. additionis added to the residue
  5. customthe mixture is reacted at room temperature for three hours
  6. filtrationthe precipitated crystals are collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-80f738ed2e534b59b7317279689bae6c
Source dataset
uspto-grants-1998_04
Patent number
US05739333

Reaction notes

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