1,1'-Thiocarbonyldi-2(1H)-pyridone → 2-Chloro-5-isothiocyanatopyrazine

HRID 2059823Notes

Reaction equation

HRID 2059823 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[C:9](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:10]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[N:6][C:5]([N:8]=[C:9]=[S:10])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 128084192-Amino-5-chloropyrazine

Product 1

HCID 575168812-Chloro-5-isothiocyanatopyrazineYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-chloropyrazin-2-amine (12.95 g, 100 mmol) and 1,1′-thiocarbonyldipyridin-2(1H)-one (27.9 g, 120 mmol) was stirred in DCM (200 mL) at room temperature for 1 h. The reaction was concentrated to ca. 100 mL volume and filtered through a pad of silica gel (1 L), washing with 10% EtOAc in hexanes. The filtrate was concentrated and dried to afford 2-chloro-5-isothiocyanatopyrazine (14.32 g, 83 mmol, 83% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 8.38 (d, J=1.26 Hz, 1H) 8.18 (d, J=1.26 Hz, 1H). MS (LC/MS) R.T.=1.84; [M+H]+=172.09.

Workup

  1. concentrationThe reaction was concentrated to ca. 100 mL volume
  2. filtrationfiltered through a pad of silica gel (1 L)
  3. washwashing with 10% EtOAc in hexanes
  4. concentrationThe filtrate was concentrated
  5. customdried

Sources & evidence

ORD record
ord-6985dca712c24ee0b275afca6e7d9bf3
Source dataset
uspto-grants-2012_10
Patent number
US08278320B2

Reaction notes

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