2-Chloro-6-methylpyridine-3-carbonitrile → HCID 178425618, compound

HRID 923635Notes

Reaction equation

HRID 923635 reaction equation
Cl[C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].NC(N)=[S:13]>C(O)CCC>[SH:13][C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 5204002-Chloro-6-methylpyridine-3-carbonitrileHCID 2723790Thiourea

Product 1

HCID 178425618HCID 178425618, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2-chloro-6-methylnicotinonitrile (220 mg, 1.45 mmol) and thiourea (348 mg, 4.57 mmol) was heated at reflux (118° C.) in n-butanol for 4 h. After cooling to room temperature, the yellow solution turned to a suspension containing light yellow solids. The solids were collected by filtration, rinsed with n-butanol, and dried in vacuo to give 2-mercapto-6-methylnicotinonitrile (218 mg, 100% yield). C7H6N2S; yellow powder; 1H NMR (400 MHz, CDCl3) δ 7.97 (1H, dt, J=8, 0.8 Hz), 7.79 (1H, dt, J=8, 0.8 Hz), 7.70 (1H, td, J=8, 1.2 Hz), 7.46 (1H, td, J=8, 1.2 Hz), 4.64 (2H, s); 13C NMR (100 MHz, CDCl3) δ 177.39, 154.77, 144.83, 117.1, 113.3, 112.7, 19.2; ESI-HRMS (negative mode) calcd for C7H5N2S: 149.0173. found: m/z 149.0172 [M−H]−.

Workup

  1. temperaturewas heated
  2. additioncontaining light yellow solids
  3. filtrationThe solids were collected by filtration
  4. washrinsed with n-butanol
  5. customdried in vacuo

Sources & evidence

ORD record
ord-6a3ad00e02d74bad94854446652ce3fb
Source dataset
uspto-grants-2016_03
Patent number
US09278982B2

Reaction notes

Loading…