1,1'-Carbonyldiimidazole → HCID 57991920, compound

HRID 2075333Notes

Reaction equation

HRID 2075333 reaction equation
[Cl:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[S:8][C:9]([C:11]([OH:13])=O)=[CH:10][C:3]=12.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:26][NH:27][C:28]([NH2:30])=[S:29]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[S:8][C:9]([C:11]([NH:26][NH:27][C:28]([NH2:30])=[S:29])=[O:13])=[CH:10][C:3]=12

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 2723789ThiosemicarbazideHCID 185161084-Chlorothieno[2,3-c]pyridine-2-carboxylic acid

Product 1

HCID 57991920HCID 57991920, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

4-Chlorothieno[2,3-c]pyridine-2-carboxylic acid (4.2 g, 19.7 mmol) was dissolved in 110 mL DMF in a round bottom flask. To this flask was added CDI (7.68 g, 47.4 mmol). After the flask was heated at 70° C. for 30 minutes, thiosemicarbazide (4.32 g, 47.4 mmol) dissolved in 5 mL DMF was added and the resulting mixture was heated at 70° C. for 30 minutes. After removing the DMF under reduced pressure, the remaining residue was mixed with 50 mL 1N HCl. After filtration and washing with water, the product was dried in a vacuum oven at 80° C. for 4 hours. The resulting product (6.0 g) was used directly in the next step. LCMS (API-ES) m/z (%): 287.1 (100%, M++H).

Workup

  1. additionwas added
  2. temperaturethe resulting mixture was heated at 70° C. for 30 minutes
  3. customAfter removing the DMF under reduced pressure
  4. additionthe remaining residue was mixed with 50 mL 1N HCl
  5. filtrationAfter filtration
  6. washwashing with water
  7. customthe product was dried in a vacuum oven at 80° C. for 4 hours

Sources & evidence

ORD record
ord-037c22bdd4e64189ad0595131106d543
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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