Thionyl Chloride → 1-(1H-Benzo[d][1,2,3]triazol-1-yl)but-3-en-1-one

HRID 1471926Notes

Reaction equation

HRID 1471926 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.[C:14](O)(=[O:18])[CH2:15][CH:16]=[CH2:17]>ClCCl>[N:5]1([C:14](=[O:18])[CH2:15][CH:16]=[CH2:17])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[N:6]1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 327433-Butenoic acidHCID 178418385HCID 178418385, compound

Product 1

HCID 673843391-(1H-Benzo[d][1,2,3]triazol-1-yl)but-3-en-1-oneYield 47.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfurous dichloride (6.91 g, 58.1 mmol) was added to a stirred solution of 1H-benzo[d][1,2,3]triazole (27.7 g, 232 mmol) in anhydrous dichloromethane (100 mL) at room temperature under argon atmosphere. The mixture was stirred for 30 min and but-3-enoic acid (5.0 g, 58.1 mmol) was added in one portion and stirring was continued for 2 h. The resulting suspension was filtered off and washed with 2.0 M NaOH (3×50 mL), dried over MgSO4, and purified by column chromatography to give the title compound as white solid (5.12 g). LCMS m/z=188.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 4.24 (d, J=6.57 Hz, 2H), 5.28-5.42 (m, 2H), 6.04-6.19 (m, 1H), 7.61 (t, J=7.71 Hz, 1H), 7.78 (t, J=7.71 Hz, 1H), 8.24 (dd, J=10.61, 8.34 Hz, 2H).

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. filtrationThe resulting suspension was filtered off
  4. washwashed with 2.0 M NaOH (3×50 mL)
  5. dry with materialdried over MgSO4
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-cb101230bd6a4a5da110977a436f7870
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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