Sulfuric Acid → 4-(4-Methyl-5-quinolin-6-yl-4H-[1,2,4]triazol-3-ylsulfanyl)-butyraldehyde

HRID 33230Notes

Reaction equation

HRID 33230 reaction equation
CC1(C)CO[CH:5]([CH2:8][CH2:9][CH2:10][S:11][C:12]2[N:13]([CH3:27])[C:14]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[N:23]=[CH:22][CH:21]=[CH:20]4)=[N:15][N:16]=2)[O:4]C1.S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:27][N:13]1[C:14]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[CH:22][CH:21]=[CH:20]3)=[N:15][N:16]=[C:12]1[S:11][CH2:10][CH2:9][CH2:8][CH:5]=[O:4]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 69313151HCID 69313151, compound

Product 1

HCID 865941734-(4-Methyl-5-quinolin-6-yl-4H-[1,2,4]triazol-3-ylsulfanyl)-butyraldehydeYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-{5-[3-(5,5-Dimethyl-[1,3]dioxan-2-yl)-propylsulfanyl]-4-methyl-4H-[1,2,4]triazol-3-yl}-quinoline (0.51 g, 1.28 mmol) was heated in water (30 ml) and sulphuric acid (1.92 mmol) at 100° C. for 3 h. The mixture was cooled and basified with sodium carbonate. The aqueous mixture was extracted with dichloromethane (3×50 ml) and the combined organic portions were dried (Na2SO4), filtered and evaporated to give the title compound as a colourless oil (0.38 g, 95%).

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe aqueous mixture was extracted with dichloromethane (3×50 ml)
  3. dry with materialthe combined organic portions were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-2174f676b65446ef9dd8a6e4d0ff4ffd
Source dataset
uspto-grants-2008_09
Patent number
US07429579B2

Reaction notes

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