Dimethylformamide → 2-(Chloromethyl)-5-(4-chlorophenyl)-4-cyclopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714671Notes

Reaction equation

HRID 714671 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:16]3[CH2:18][CH2:17]3)[C:10](=[O:15])[N:11]([CH2:13]O)[N:12]=2)=[CH:4][CH:3]=1.CN(C=O)C.S(Cl)([Cl:26])=O.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:26][CH2:13][N:11]1[C:10](=[O:15])[N:9]([CH:16]2[CH2:18][CH2:17]2)[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:12]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 674118375-(4-Chlorophenyl)-4-cyclopropyl-2-(hydroxymethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 674116472-(Chloromethyl)-5-(4-chlorophenyl)-4-cyclopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

875 mg (3.29 mmol) of the compound from Example 121A were suspended in 3 ml of dichloromethane, and a drop of DMF and 288 μl (3.95 mmol) of thionyl chloride were added. The mixture was stirred at RT for 3 h. For work-up, 5 ml of saturated aqueous sodium bicarbonate solution were added. The mixture was extracted once with 10 ml of tert-butyl methyl ether. The organic phase was washed once with 5 ml of water, dried over sodium sulfate, filtered and concentrated under reduced pressure. Drying of the residue under high vacuum gave 803 mg (86% of theory) of the target compound.

Workup

  1. extractionThe mixture was extracted once with 10 ml of tert-butyl methyl ether
  2. washThe organic phase was washed once with 5 ml of water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customDrying of the residue under high vacuum
  7. customgave 803 mg (86% of theory) of the target compound

Sources & evidence

ORD record
ord-278cb5e3d5c64f148caad1a3a0d87355
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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