2-Chloro-4,6-dimethyl-3-pyridinecarbonitrile → HCID 178425247, compound

HRID 923636Notes

Reaction equation

HRID 923636 reaction equation
Cl[C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[C:4]#[N:5].NC(N)=[S:14]>C(O)CCC>[SH:14][C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 2232612-Chloro-4,6-dimethyl-3-pyridinecarbonitrileHCID 2723790Thiourea

Product 1

HCID 178425247HCID 178425247, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2-chloro-4,6-dimethylnicotinonitrile (800 mg, 4.83 mmol) and thiourea (1.2 kg, 15.76 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-4,6-dimethylnicotinonitrile (778 mg, 98% yield). C8H8N2S; light yellow powder; mp 219-221° C.; 1H NMR (400 MHz, CDCl3) δ 6.40 (1H, s), 2.45 (3H, s), 2.43 (3H, s); ESI-HRMS (negative mode) calcd for C8H7N2S: 163.0330. found: m/z 163.0332 [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-7ddfe38c21d94379b7d50738fc8c95d3
Source dataset
uspto-grants-2016_03
Patent number
US09278982B2

Reaction notes

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