Iodine → HCID 178483141, compound

HRID 2078755Notes

Reaction equation

HRID 2078755 reaction equation
[CH3:1][N:2]([CH3:12])[CH2:3][C:4]1[S:11][C:10]2[CH:9]=[N:8][NH:7][C:6]=2[CH:5]=1.[I:13]I.[OH-].[K+].S(=O)(O)[O-].[Na+]>CN(C)C=O.O>[I:13][C:9]1[C:10]2[S:11][C:4]([CH2:3][N:2]([CH3:12])[CH3:1])=[CH:5][C:6]=2[NH:7][N:8]=1

Participants

7

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 23665763Sodium BisulfiteHCID 57637329HCID 57637329, compound2×

Product 1

HCID 178483141HCID 178483141, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To dimethyl-(1H-thieno[3,2-c]pyrazol-5-ylmethyl)-amine [1 g, 5.51 mmol, Intermediate (5)] in solution in dimethylformamide (10 mL) is added iodine (2.1 g, 8.3 mmol) and potassium hydroxide (0.930 g, 16.5 mmol). The dark solution is stirred at room temperature for 5 hours. Sodium bisulfite (1.5 g) in solution in water is added. The resulting suspension is extracted twice with ethyl acetate. The organic layer is dried over magnesium sulfate and concentrated. The residue is chromatographed through silica gel (ethyl acetate-1.0M ammonia in methanol, 90:10 as eluant) to produce (3-iodo-1H-thieno[3,2-c]pyrazol-5-ylmethyl)-dimethyl-amine [0.87 g, 51%, Intermediate (6)] as a beige powder. LC/MS: RT=1.20 minutes, 307.98 m/e (M+H).

Workup

  1. extractionThe resulting suspension is extracted twice with ethyl acetate
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue is chromatographed through silica gel (ethyl acetate-1.0M ammonia in methanol, 90:10 as eluant)

Sources & evidence

ORD record
ord-137fd7f0f9eb4cf4975973dd9be6b976
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

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