3-Methylthiopropionate → 1-(1H-benzo[d][1,2,3]triazol-1-yl)-3-(methylthio)propan-1-one

HRID 1471929Notes

Reaction equation

HRID 1471929 reaction equation
S(Cl)(Cl)=O.[NH:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[N:6]1.[CH3:14][S:15][CH2:16][CH2:17][C:18](O)=[O:19]>ClCCl>[N:5]1([C:18](=[O:19])[CH2:17][CH2:16][S:15][CH3:14])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[N:6]1

Participants

5

Reactant 3

HCID 5633-MethylthiopropionateHCID 24386Thionyl ChlorideHCID 178418385HCID 178418385, compound

Product 1

HCID 673854071-(1H-benzo[d][1,2,3]triazol-1-yl)-3-(methylthio)propan-1-oneYield 55.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfurous dichloride (4.95 g, 41.6 mmol) was added to a stirred solution of 1H-benzo[d][1,2,3]triazole (19.83 g, 166 mmol) in anhydrous dichloromethane (300 mL) at room temperature under argon. The mixture was stirred for 30 min and 3-(methylthio)propanoic acid (5.0 g, 41.6 mmol) was added in one portion and stirring was continued for 2 h. The resulting suspension was filtered off and the filtrated was washed with 2 M NaOH (3×50 mL), dried over MgSO4, and purified by column chromatography to give the title compound as clear oil (5.12 g). LCMS m/z=222.1 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 2.21 (s, 3H), 3.05 (t, J=7.07 Hz, 2H), 3.74 (t, J=7.07 Hz, 2H), 7.42-7.54 (m, 1H), 7.56-7.69 (m, 1H), 8.08 (d, J=8.34 Hz, 1H), 8.24 (d, J=8.08 Hz, 1H).

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. filtrationThe resulting suspension was filtered off
  4. washthe filtrated was washed with 2 M NaOH (3×50 mL)
  5. dry with materialdried over MgSO4
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-a6a1fcc1bd0845fd8e9b4d5e9fe2a209
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

Loading…