HCID 90460960, compound → HCID 90461353, compound

HRID 2202115Notes

Reaction equation

HRID 2202115 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[N:5][S:6][N:7]=1>ClCCl.O=[Mn]=O>[CH:2]([C:3]1[C:4]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[N:5][S:6][N:7]=1)=[O:1]

Participants

4

Reactant 1

HCID 90460960HCID 90460960, compound

Product 1

HCID 90461353HCID 90461353, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-[4-(hydroxymethyl)-1,2,5-thiadiazol-3-yl]benzonitrile (230 mg, 1.06 mmol, 1.00 equiv) and MnO2 (922 mg, 10.61 mmol, 10.02 equiv) in dichloromethane (20 mL) was stirred at 40° C. for 1.5 h. The reaction was cooled to room temperature and the solids were removed by filtration. The filtrate was concentrated under vacuum and the residue was purified on a silica gel column eluted with 2.5-5% of ethyl acetate in petroleum ether to give 113 mg (50%) of 4-(4-formyl-1,2,5-thiadiazol-3-yl)benzonitrile as a white solid. 1H-NMR (300 MHz, CDCl3): δ 10.34 (s, 1H), 8.00 (d, J=8.4 Hz, 1H), 7.80 (d, J=8.1 Hz, 1H) ppm.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe solids were removed by filtration
  3. concentrationThe filtrate was concentrated under vacuum
  4. customthe residue was purified on a silica gel column
  5. washeluted with 2.5-5% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-98f5176656804d3686b56b02fc65fcec
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

Loading…