Thionyl Chloride → HCID 21283340, compound

HRID 2232223Notes

Reaction equation

HRID 2232223 reaction equation
O[CH2:2][CH2:3][CH2:4][N:5]([CH3:27])[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]2=[N:16][N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[N:8]2[N:7]=1.S(Cl)([Cl:30])=O>C(Cl)(Cl)Cl.CN(C)C=O>[Cl:30][CH2:2][CH2:3][CH2:4][N:5]([CH3:27])[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]2=[N:16][N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[N:8]2[N:7]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 21283338HCID 21283338, compound

Product 1

HCID 21283340HCID 21283340, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent2×

Procedure

To 2.8 g of N-(3-hydroxypropyl)-N-methyl-3-(4-methoxy phenyl)-1,2,4-triazolo[3,4-a]phthalazin-6-amine (the compound of example 32) dissolved in chloroform (30 ml) are added a few drops of N,N-dimethylformamide and then 1.1 ml of thionyl chloride in chloroform (5 ml). The mixture is refluxed for about 5 hours. After cooling to room temperature, the mixture is concentrated to dryness and the residue is taken up with cold aqueous sodium bicarbonate. The product of the title is collected after filtration and crystallized from ethanol. Yield 85%. M.p. 113°-115° C.

Workup

  1. temperatureThe mixture is refluxed for about 5 hours
  2. concentrationthe mixture is concentrated to dryness
  3. customThe product of the title is collected
  4. filtrationafter filtration
  5. customcrystallized from ethanol

Sources & evidence

ORD record
ord-d2e8a8714c7549b4b116a124db51c0ae
Source dataset
uspto-grants-1988_11
Patent number
US04788186

Reaction notes

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