Iodine → HCID 178506571, compound
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]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
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
- extractionIt is extracted twice with diethyl ether
- dry with materialThe combined organic layers are dried over magnesium sulfate
- concentrationconcentrated
- 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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