Triethylamine → 3-chloro-5-methylpyrazine-2-carbonitrile

HRID 235074Notes

Reaction equation

HRID 235074 reaction equation
[CH3:1][C:2]1[NH:8][C:6](=O)[C:5](NC=O)=[N:4][CH:3]=1.C([N:14]([CH2:17]C)CC)C.O=P(Cl)(Cl)[Cl:21]>>[C:17]([C:5]1[C:6]([Cl:21])=[N:8][C:2]([CH3:1])=[CH:3][N:4]=1)#[N:14]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 54101360HCID 54101360, compound

Product 1

HCID 2924673-chloro-5-methylpyrazine-2-carbonitrileYield 77%

Procedure

3-Carboxamido-2-hydroxy-6-methylpyrazine (4.09 g, 26.70 mmol), prepared by the method of Dick and Wood, J. Chem. Soc.,1379 (1955), was treated as described in Example 91A with triethylamine (5.41 g, 53.41 mmol) and 70 ml POCl3 to yield the title compound (3.16 g, 77%) as a fluffy yellow solid. mp: 63°-65° C. 1H NMR (300 MHz, CDCl3) δ2.70 (s, 3H), 8.50 (s, 1H). MS (DCI/NH3) m/e 171 (M+NH4)+.

Workup

  1. additionSoc.,1379 (1955), was treated

Sources & evidence

ORD record
ord-422dd9f6a1e248e0b65b94f8b12f94db
Source dataset
uspto-grants-1997_01
Patent number
US05597823

Reaction notes

Loading…