Methyl isothiocyanate → HCID 67027559, compound

HRID 455148

Reaction equation

HRID 455148 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH2:17][C:18]([NH:20][NH2:21])=O)=[CH:4][CH:3]=1.[N:22]([CH3:25])=[C:23]=[S:24]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH2:17][C:18]2[S:24][C:23]([NH:22][CH3:25])=[N:21][N:20]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 670291592-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)acetohydrazide

Product 1

HCID 67027559HCID 67027559, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(2-(4-chlorophenyl)imidazo[1,2-α]pyridin-3-yl)acetohydrazide (0.1 g, 0.33 mmol) in EtOH (1 mL) was treated with isothiocyanatomethane (0.023 mL, 0.33 mmol) and refluxed for 3 h. The precipitated thiosemicarbazide was filtered and dissolved in concentrated sulfuric acid. The reaction mixture was stirred for 30 min at rt. The mixture was poured into cold water and the precipitated product was filtered in vacuo and washed with ditilled water. The crude product was recrystallized in EtOH to provide the title product as a yellow solid. M/e+ 356 for C17H15ClN5S (M+H)+; 1H-NMR (400 MHz, CDCl3) δ 8.15 (d, J=6.9 Hz, 1H), 7.71 (d, J=8.4 Hz, 2H), 7.63 (d, J=9.1 Hz, 1H), 7.45 (d, J=8.4 Hz, 2H), 7.22 (m, 2H), 6.84 (t, J=6.6 Hz, 1H), 4.65 (s, 2H), 2.98 (s, 3H) ppm.

Workup

  1. temperaturerefluxed for 3 h
  2. filtrationThe precipitated thiosemicarbazide was filtered
  3. dissolutiondissolved in concentrated sulfuric acid
  4. additionThe mixture was poured into cold water
  5. filtrationthe precipitated product was filtered in vacuo
  6. washwashed with ditilled water
  7. customThe crude product was recrystallized in EtOH

Sources & evidence

ORD record
ord-888b828b65714ecd81476971290fd73e
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Linked notes

Loading…