Phosphorus oxychloride → 4-Chloro-2-(methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine

HRID 1261920Notes

Reaction equation

HRID 1261920 reaction equation
[CH3:1][S:2][C:3]1[NH:8][C:7](=O)[C:6]2=[CH:10][CH:11]=[CH:12][N:5]2[N:4]=1.P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:7]1[C:6]2=[CH:10][CH:11]=[CH:12][N:5]2[N:4]=[C:3]([S:2][CH3:1])[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1357420592-(Methylthio)pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 378183844-Chloro-2-(methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine

Conditions

Temperature
75 °C

Procedure

2-Methylsulfanyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (23.25 g, 0.1283 mol) was dissolved in Phosphoryl chloride (114 mL, 1.22 mol) and the reaction was then heated at 75° C. until HPLC showed consumption of starting material. The mixture was reduced and the solution was poured over ice. The solid was then filtered and washed with water to afford the desired product. The product was then allowed to dry under vacuum overnight to provide 25.47 grams of 4-Chloro-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine as a yellow solid. 1H NMR (400 MHz, DMSO, d6) δ 8.16 (s, 1H), 7.05 (m, 1H), 6.98 (m, 1H), 2.55 (s, 3H).

Workup

  1. customconsumption of starting material
  2. additionthe solution was poured over ice
  3. filtrationThe solid was then filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-3c947e3b8bdb4acea005ef4e3d679dd5
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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