Iodine → HCID 178497021, compound

HRID 2078701Notes

Reaction equation

HRID 2078701 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:12][C:11]2[CH:10]=[N:9][N:8](C(=O)C)[C:7]=2[CH:6]=1)=[O:4].C[O-].[Na+].[I:19]I>CO.CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[S:12][C:11]2[C:10]([I:19])=[N:9][NH:8][C:7]=2[CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 807IodineHCID 10942334Sodium MethoxideHCID 57637373Methyl 1-acetyl-1H-thieno[3,2-c]pyrazole-5-carboxylate2×

Product 1

HCID 178497021HCID 178497021, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 1-acetyl-1H-thieno[3,2-c]pyrazole-5-carboxylic acid methyl ester [1.3 g, 5.79 mmol, Intermediate (25)] in methanol (30 mL) is added sodium methoxide (25 wt % in methanol). The resulting solution mixture is stirred at 60° C. oil bath for 20 minutes. The oil bath is removed and stirred for 5 minutes. To this is added a solution of iodine (1.76 g, 6.93 mmol) in dimethyl formamide (2 mL). The reaction mixture then heated to 60° C. for 1 hour. The solvent is removed in vacuo. The crude is partitioned between ethyl acetate (100 mL) and water (100 mL) and aqueous layer is further extracted with twice ethyl acetate (25 mL). The combined ethyl acetate phases are washed with brine, dried over sodium sulfate and filtered. The solvent is removed in vacuo to give 3-iodo-1H-thieno[3,2-c]pyrazole-5-carboxylic acid methyl ester [1.58 g, 89%, Intermediate (26)] as light yellow solid; 1H NMR [(CD3)2SO)]: δ 13.80 (1H, brs, NH), 7.947 (1H, s), 3.870 (3H, s).

Workup

  1. customThe oil bath is removed
  2. stirringstirred for 5 minutes
  3. temperatureThe reaction mixture then heated to 60° C. for 1 hour
  4. customThe solvent is removed in vacuo
  5. customThe crude is partitioned between ethyl acetate (100 mL) and water (100 mL) and aqueous layer
  6. extractionis further extracted with twice ethyl acetate (25 mL)
  7. washThe combined ethyl acetate phases are washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-b1e0c9b840d64b179ed0fa87a3802753
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

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