Water → HCID 15434275, compound

HRID 841916Notes

Reaction equation

HRID 841916 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][N:16]=2)[CH2:11][CH2:10]1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1.C(OCC)C.O>C1(C)C=CC=CC=1>[C:1]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][N:16]=2)[CH2:11][CH2:10]1)(=[S:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 87949Lawesson's reagentHCID 6919148HCID 6919148, compound

Product 1

HCID 15434275HCID 15434275, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

0.56 g (1.9 mmol) of 2-(4-benzoyl-1-piperazinyl)-4-methoxypyrimidine are dissolved in 25 mL of dry toluene, and 0.46 g (1.14 mmol) of Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,32,4-dithiadiphosphaethano-2,4-disulphide) added. The mixture is heated to 80-90° C. for 16 hours. Ethyl ether is added, basic water is used to wash the residue and the organic extract is dried with NaSO4 and the solvent evaporated off under reduced pressure. The resulting crude residue is crystallised with ethyl ether-petroleum ether to give 160 mg (0.5 mmol) of 2-(4-thiobenzoyl-1-piperazinyl)-4-methoxypyrimidine. m.p.=125-129° C.

Workup

  1. washto wash the residue
  2. extractionthe organic extract
  3. dry with materialis dried with NaSO4
  4. customthe solvent evaporated off under reduced pressure
  5. customThe resulting crude residue is crystallised with ethyl ether-petroleum ether

Sources & evidence

ORD record
ord-7341554352ab4d4796276e4a14f85c78
Source dataset
uspto-grants-2002_04
Patent number
US06372746B1

Reaction notes

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