N-Iodosuccinimide → HCID 178477918, compound

HRID 1296935Notes

Reaction equation

HRID 1296935 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([Cl:23])=[CH:11][C:10]=1[C:24]1[CH:28]=[CH:27][NH:26][N:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:29]N1C(=O)CCC1=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([Cl:23])=[CH:11][C:10]=1[C:24]1[C:28]([I:29])=[CH:27][NH:26][N:25]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178477876HCID 178477876, compound

Product 1

HCID 178477918HCID 178477918, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-(2,4-bis-benzyloxy-5-chloro-phenyl)-1H-pyrazole (4.06 g 10.05 mmol) in DCM (50 ml) was added N-iodosuccinimide (2.35 g, 10.45 mmol) in bulk. The mixture was stirred at room temperature for two hours and then partitioned between water and DCM. The organics were washed with saturated sodium thiosulphate solution then water and dried in vacuo to give a yellow crystalline mass, which was triturated from ethyl acetate by the gradual addition, whilst stirring, of hexanes to give 3-(2,4-bis-benzyloxy-5-chloro-phenyl)-4-iodo-1H-pyrazole (5.21 g, 97%).

Workup

  1. custompartitioned between water and DCM
  2. washThe organics were washed with saturated sodium thiosulphate solution
  3. dry with materialwater and dried in vacuo
  4. customto give a yellow crystalline mass, which
  5. customwas triturated from ethyl acetate by the gradual addition
  6. stirringwhilst stirring, of hexanes

Sources & evidence

ORD record
ord-31137a5a8c0743368bd42cea135c7731
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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