Phosphorus oxychloride → HCID 178426706, compound

HRID 1184886Notes

Reaction equation

HRID 1184886 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][C:12]([C:14]1[S:22][C:17]2=[N:18][CH:19]=[CH:20][N:21]=[C:16]2[CH:15]=1)=O.P(Cl)(Cl)([Cl:25])=O>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1/[N:11]=[C:12](\[Cl:25])/[C:14]1[S:22][C:17]2=[N:18][CH:19]=[CH:20][N:21]=[C:16]2[CH:15]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67125678N-(2-methyl-5-nitrophenyl)thieno[2,3-b]pyrazine-6-carboxamide

Product 1

HCID 178426706HCID 178426706, compoundYield 112%

Procedure

A solution of N-(2-methyl-5-nitrophenyl)thieno[2,3-b]pyrazine-6-carboxamide 75 (400 mg, 1.273 mmol) in phosphorus oxychloride (15 mL, 161 mmol) was stirred at 105° C. for 7 h. POCl3 was evaporated to dryness and co evaporated with toluene. Triturating with acetonitrile gave crude (Z)—N-(2-methyl-5-nitrophenyl)thieno[2,3-b]pyrazine-6-carbimidoyl chloride 76 (474 mg, 112%) which was used without further purification. (m/z)=333 (M+H)+.

Workup

  1. customPOCl3 was evaporated to dryness and co
  2. customevaporated with toluene
  3. customTriturating with acetonitrile

Sources & evidence

ORD record
ord-b34c7573e7634d98b4b25fc88e6ea613
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

Loading…