Iodine → HCID 178506571, compound

HRID 2078683Notes

Reaction equation

HRID 2078683 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][S:8][C:4]=2[CH:3]=[N:2]1.[I:9]I.[OH-].[K+].S(=O)(O)[O-].[Na+]>CN(C)C=O.O>[I:9][C:3]1[C:4]2[S:8][CH:7]=[CH:6][C:5]=2[NH:1][N:2]=1

Participants

7

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 219154291H-Thieno[3,2-c]pyrazoleHCID 23665763Sodium Bisulfite

Product 1

HCID 178506571HCID 178506571, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-thieno[3,2-c]pyrazole (160 mg, 1.29 mmol) and iodine (490 mg, 1.94 mmol) in dimethyl formamide (5 mL) is added potassium hydroxide (220 mg, 3.87 mmol). The mixture is stirred at room temperature for 30 minutes. A solution of sodium bisulfite (200 mg) in water (2 mL) is then added. It is extracted twice with diethyl ether. The combined organic layers are dried over magnesium sulfate and concentrated. The residue is chromatographed (n-heptane-ethyl acetate, 90:100) to afford 195 mg (60%) of 3-iodo-1H-thieno[3,2-c]pyrazole as a beige powder. LC/MS: RT=2.50 minutes, 250.90 m/e (M+1).

Workup

  1. extractionIt is extracted twice with diethyl ether
  2. dry with materialThe combined organic layers are dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue is chromatographed (n-heptane-ethyl acetate, 90:100)

Sources & evidence

ORD record
ord-906751fb46864f43b3924914090f2381
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

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