Phenyl Isothiocyanate → HCID 178527841, compound

HRID 1354568Notes

Reaction equation

HRID 1354568 reaction equation
[C:1]1([N:7]=[C:8]=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10]CC1C=CC=CN=1>>[CH:1]1[N:7]=[C:8]([SH:9])[N:10]2[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=12

Participants

3

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 195092-Pyridinemethanamine

Product 1

HCID 178527841HCID 178527841, compound

Procedure

Phenyl Isothiocyanate (22 mL, 0.184 mol) is added slowly to a solution of 2-(aminomethyl)-pyridine (19 mL, 0.184 mol) in xylenes (180 mL) with cooling on ice. The resulting solution is heated at reflux for 3 h, and then allowed to cool to RT overnight. The resulting suspension is cooled to 0° C. and the solid is collected by filtration. The solid is washed with toluene and ether, and dried under vacuum to yield imidazo[1,5-a]pyridine-3-thiol as a green solid: 1H-NMR (CDCl3) δ 12.9 (br s, 1H), 8.25 (dd, J=7.5, 0.9, 1H), 7.21 (d, J=9.3, 1H), 7.06 (s, 1H), 6.75 (dd, J=9.3, 6.3, 1H), 6.59 (dt, J=7.5, 0.9); MS (M+1)+ 151.

Workup

  1. temperaturewith cooling on ice
  2. temperatureThe resulting solution is heated
  3. temperatureat reflux for 3 h
  4. temperatureThe resulting suspension is cooled to 0° C.
  5. filtrationthe solid is collected by filtration
  6. washThe solid is washed with toluene and ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-67e31fd8b5d84c70a6ff9e59af10a554
Source dataset
uspto-grants-2007_05
Patent number
US07223866B2

Reaction notes

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