Sodium hydride → HCID 19896204, compound

HRID 1196767Notes

Reaction equation

HRID 1196767 reaction equation
[NH2:1][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15])=[CH:3][C:4]([O:6]CC)=O.[H-].[Na+].[CH3:18][O:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29](=O)[O:30]CC)=[CH:24][CH:23]=1>CN(C)C=O>[CH3:18][O:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[C:4](=[O:6])[CH:3]=[C:2]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[Cl:15])[NH:1][C:29]2=[O:30])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 19896200HCID 19896200, compoundHCID 67836558HCID 67836558, compound

Product 1

HCID 19896204HCID 19896204, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

8.7 g of ethyl 3-amino-3-(2-chlorophenyl)-2-propenoate was added dropwise to a 40 ml dimethylformamide of 1.8 g of sodium hydride (purity: 55%) with stirring at 0° C. The solution was stirred at room temperature for 15 minutes, cooled to 0° C. and added dropwise with a 20 ml dimethylformamide solution of 7.2 g of ethyl 4-methoxymethoxyphenylcarbamate. After stirring the solution at 120° C. for 2 hours, the solvent was distilled away under reduced pressure. The residue was dissolved with 200 ml of water and washed with diethyl ether. The obtained aqueous layer was added into a mixed solution of 50 ml of concentrated hydrochloric acid and 150 g of ice. The precipitated crystals were filtered out and dried under reduced pressure to obtain 10.0 g of 3-(4-methoxymethoxyphenyl)-6-(2-chlorophenyl)-2,4(1H,3H)-pyrimidinedione.

Workup

  1. stirringThe solution was stirred at room temperature for 15 minutes
  2. temperaturecooled to 0° C.
  3. stirringAfter stirring the solution at 120° C. for 2 hours
  4. distillationthe solvent was distilled away under reduced pressure
  5. dissolutionThe residue was dissolved with 200 ml of water
  6. washwashed with diethyl ether
  7. additionThe obtained aqueous layer was added into a mixed solution of 50 ml of concentrated hydrochloric acid and 150 g of ice
  8. filtrationThe precipitated crystals were filtered out
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-391f621f7e544323bc739ae84833a71e
Source dataset
uspto-grants-1992_05
Patent number
US05116404

Reaction notes

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