Water → 5-Isothiocyanato-3-methylpicolinonitrile

HRID 515787Notes

Reaction equation

HRID 515787 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH2:5][C:6]1[CH:7]=[C:8]([CH3:14])[C:9]([C:12]#[N:13])=[N:10][CH:11]=1.O>C(Cl)(Cl)Cl>[N:5]([C:6]1[CH:7]=[C:8]([CH3:14])[C:9]([C:12]#[N:13])=[N:10][CH:11]=1)=[C:1]=[S:2]

Participants

5

Reactant 3

HCID 962WaterHCID 10040ThiophosgeneHCID 218645665-Amino-3-methylpyridine-2-carbonitrile2×

Product 1

HCID 580972105-Isothiocyanato-3-methylpicolinonitrileYield 82.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thiophosgene (0.24 mL, 3.1 mmol) was added to a stirred biphasic solution of 5-amino-3-methylpicolinonitrile (Intermediate 2, 275 mg, 2.07 mmol) in CHCl3 (6 mL)/water (10 mL) and the resulting orange mixture was stirred at room temperature overnight. The two layers were separated and the aqueous layer was extracted with DCM (3×). The organics were combined, washed with a saturated solution of sodium bicarbonate (2×), dried over sodium sulfate, and evaporated to dryness to afford 300 mg of 5-isothiocyanato-3-methylpicolinonitrile as an orange solid. 1H NMR (300 MHz, DMSO-d6) δ 8.66 (s, 1H), 8.06 (s, 1H), 2.5 (s, 3H).

Workup

  1. customThe two layers were separated
  2. extractionthe aqueous layer was extracted with DCM (3×)
  3. washwashed with a saturated solution of sodium bicarbonate (2×)
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-c324d03c81f04d068887e378c246740f
Source dataset
uspto-grants-2015_08
Patent number
US09108944B2

Reaction notes

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