N-Iodosuccinimide → HCID 21083717, compound

HRID 348000Notes

Reaction equation

HRID 348000 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[CH:10]=[C:6]2[N:5]=[CH:4][CH:3]=1.[I:18]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.C(Cl)Cl>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:10]([I:18])=[C:6]2[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 210837197-Chloro-2-(2-chlorophenyl)-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 21083717HCID 21083717, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-chloro-2-(2-chlorophenyl)-pyrazolo[1,5-a]pyrimidine (I-1A-1c; 6.00 g, 22.7 mmol) in chloroform (23 ml) and methylene chloride (207 ml) cooled in an ice bath was added N-iodosuccinimide (7.67 g, 34.1 mmol), portionwise. The ice bath was removed and the reaction was stirred overnight at room temperature. After concentrating the red-brown reaction, in vacuo, an ethyl acetate solution of the residue was washed with saturated aqueous Na2S2O4 and brine. The solution was dried (MgSO4), concentrated, in vacuo, and the resulting solids repulped at room temperature from ethyl acetate (30 ml) to give product I-1A-1d as a solid (6.8 g, 77%): +APcI MS (M+1) 390.1; 1H NMR (400 MHz, CD2Cl2) δ 8.52 (d, J=4.6 Hz, 1H), 7.59–7.56 (m, 1H), 7.53–7.42 (m, 3H), 7.14 (d, J=4.6 Hz, 1H).

Workup

  1. customThe ice bath was removed
  2. concentrationAfter concentrating
  3. customthe red-brown reaction
  4. washin vacuo, an ethyl acetate solution of the residue was washed with saturated aqueous Na2S2O4 and brine
  5. dry with materialThe solution was dried (MgSO4)
  6. concentrationconcentrated, in vacuo
  7. customrepulped at room temperature from ethyl acetate (30 ml)

Sources & evidence

ORD record
ord-d15e5fa6e04140bf8fd17ef4e170dd3f
Source dataset
uspto-grants-2007_02
Patent number
US07176210B2

Reaction notes

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