Iodine → HCID 178506571, compound

HRID 246055Notes

Reaction equation

HRID 246055 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][S:8][C:4]=2[CH:3]=[N:2]1.[OH-].[K+].[I:11]I>CN(C=O)C>[I:11][C:3]1[C:4]2[S:8][CH:7]=[CH:6][C:5]=2[NH:1][N:2]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 219154291H-Thieno[3,2-c]pyrazole

Product 1

HCID 178506571HCID 178506571, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-thieno[3,2-c]pyrazole (1.0 g, 8.05 mmol) in DMF (65 ml) at room temperature was added potassium hydroxide (1.36 g, 24.2 mmol) and iodine (3.07 g, 12.1 mmol). The maroon reaction mixture was stirred at room temperature for 3 h then quenched with 10% aqueous Na2S2O3 and diluted with water. The mixture was extracted with EtOAc (2×). The combined organics were washed with water, sat LiCl, and sat NaCl, then dried over MgSO4 and concentrated to afford 2.0 g (99%) of 3-iodo-1H-thieno[3,2-c]pyrazole as a light brown solid. 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 13.38 (br. s., 1H), 7.68 (d, J=5.3 Hz, 1H), 7.21 (d, J=5.3 Hz, 1H).

Workup

  1. customThe maroon reaction mixture
  2. customthen quenched with 10% aqueous Na2S2O3
  3. additiondiluted with water
  4. extractionThe mixture was extracted with EtOAc (2×)
  5. washThe combined organics were washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d58fd1a9fb774dc3bc5b42440bce523d
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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