p-Toluenesulfonic acid → HCID 178515487, compound

HRID 923340Notes

Reaction equation

HRID 923340 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([NH2:13])[NH:10][N:9]=2)=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[O:25]1[C:29]2[CH:30]=[CH:31][C:32]([C:34](=O)[CH2:35][C:36](OCC)=[O:37])=[CH:33][C:28]=2[O:27][CH2:26]1>C1(OC2C=CC=CC=2)C=CC=CC=1>[O:25]1[C:29]2[CH:30]=[CH:31][C:32]([C:34]3[NH:13][C:11]4[N:10]([N:9]=[C:8]([C:5]5[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=5)[N:12]=4)[C:36](=[O:37])[CH:35]=3)=[CH:33][C:28]=2[O:27][CH2:26]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 2756586Ethyl 3-(2H-1,3-benzodioxol-5-yl)-3-oxopropanoateHCID 178508293HCID 178508293, compound

Product 1

HCID 178515487HCID 178515487, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
170 °C

Procedure

To a solution of 3-(4-chlorophenyl)-1H-1,2,4-triazol-5-amine (50 mg, 0.26 mmol) in diphenyether (2 ml) was added TsOH (2.2 mg, 0.01 mmol) and ethyl 3-(benzo[d][1,3]dioxol-5-yl)-3-oxopropanoate (81 mg, 0.34 mmol). After stirring 2 h at 170° C., the reaction was quenched by the addition of hexane (5 ml), the product was collected by filtration and washed with methanol (10 ml) and dried in an oven under reduced pressure to give 5-(benzo[d][1,3]dioxol-5-yl)-2-(4-chlorophenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a off-white solid (23.1 mg, 24%).

Workup

  1. customthe reaction was quenched by the addition of hexane (5 ml)
  2. filtrationthe product was collected by filtration
  3. washwashed with methanol (10 ml)
  4. customdried in an oven under reduced pressure

Sources & evidence

ORD record
ord-30ae433dc90c4542a6920ffa4431b565
Source dataset
uspto-grants-2016_03
Patent number
US09278973B2

Reaction notes

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