Water → HCID 135974536, compound

HRID 2054410Notes

Reaction equation

HRID 2054410 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:11]2[N:12]=[CH:13][NH:14][C:15](=[O:16])[N:10]2[N:9]=1.[I:18]N1C(=O)CCC1=O.O.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([I:18])=[C:11]2[N:12]=[CH:13][NH:14][C:15](=[O:16])[N:10]2[N:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24489Sodium DithioniteHCID 120273N-IodosuccinimideHCID 135974540HCID 135974540, compound

Product 1

HCID 135974536HCID 135974536, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 7-(2-chlorophenyl)-3H-pyrazolo[1,5-a][1,3,5]-triazin-4-one (I-3A-9c; 2.59 g, 10.5 mmol) in chloroform (115 ml) cooled in an ice bath was added N-iodosuccinimide (2.36 g, 10.5 mmol), portionwise, over 15 minutes. After stirring for 3 hours, the reaction was added to stirring water and methylene chloride. A solution of saturated aqueous Na2S2O4 was added until the color remained light yellow. The solid precipitate that was dispersed in the aqueous phase was collected by vacuum filtration and then dried, in vacuo, to afford intermediate I-3A-9d as a solid (3.78 g, 97%): +APcI MS (M+1) 372.9; 1H NMR (400 MHz, CD3OD) δ 8.05 (s, 1H), 7.55-7.40 (m, 4H).

Workup

  1. temperaturecooled in an ice bath
  2. additionthe reaction was added
  3. additionThe solid precipitate that was dispersed in the aqueous phase
  4. filtrationwas collected by vacuum filtration
  5. customdried, in vacuo

Sources & evidence

ORD record
ord-611a05fe8abb4350a70fa0954864d08c
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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