Dimethylmalonyl Dichloride → HCID 11350712, compound

HRID 1935380Notes

Reaction equation

HRID 1935380 reaction equation
[CH3:1][C:2]([CH3:9])([C:6](Cl)=[O:7])[C:3](Cl)=[O:4].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH2:33])=[O:32])=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=[CH:14][CH:13]=1>S1CCCC1>[CH3:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([N:30]4[C:6](=[O:7])[C:2]([CH3:9])([CH3:1])[C:3](=[O:4])[NH:33][C:31]4=[O:32])=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 4523180Dimethylmalonyl DichlorideHCID 22464439HCID 22464439, compound

Product 1

HCID 11350712HCID 11350712, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 1127TetrahydrothiopheneSolvent

Conditions

Temperature
50 °C

Procedure

2,2-Dimethylmalonyl chloride (0.057 mol) was added to a solution of N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]urea (0.057 mol) in tetrahydrothiophene, 1,1-dioxide (200 ml). After stirring for 15 minutes, the reaction mixture was heated to 40° C. for 3 hours and at 50° C. for 2 hours. The reaction mixture was allowed to stand overnight at 25° C. The product was precipitated with diethyl ether and crystallized by trituration. The product was recrystallized from 2-propanol, yielding 20.1 g of 1-[4-[4-(4-methoxyphenyl)-1-piperazinyl)phenyl]-5,5-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione (interm. 16).

Workup

  1. waitto stand overnight at 25° C
  2. customThe product was precipitated with diethyl ether
  3. customcrystallized by trituration
  4. customThe product was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-e7a2ab052a644983a4482660b65d40a5
Source dataset
uspto-grants-2002_05
Patent number
US06387906B1

Reaction notes

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