Dimethylformamide → HCID 68293646, compound

HRID 1472778Notes

Reaction equation

HRID 1472778 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:8]([NH2:10])=O)[S:5][C:6]=1[I:7].CN(C=O)C.N1C(Cl)=NC(Cl)=NC=1Cl>O>[I:1][C:2]1[CH:3]=[C:4]([C:8]#[N:10])[S:5][C:6]=1[I:7]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7954Cyanuric chlorideHCID 68293628HCID 68293628, compound

Product 1

HCID 68293646HCID 68293646, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

An oven-dried round-bottomed flask was charged with 4,5-diiodothiophene-2-carboxamide (5.68 g, 15.0 mmol) and 20 mL of DMF under an argon atmosphere. The solution was cooled on an ice-water bath, and cyanuric chloride (1.81 g, 9.8 mmol) was then added in one portion. After stirring at 0° C. for 1 h, the reaction mixture was warmed to room temperature, and stirred for a further 3 h. 100 mL of water was added. A white solid was formed, which was collected through suction filtration, washed with water, and dried together with phosphorous pentoxide under vacuum to afford 4.87 g (90%) of product.

Workup

  1. temperatureThe solution was cooled on an ice-water bath
  2. temperaturethe reaction mixture was warmed to room temperature
  3. stirringstirred for a further 3 h
  4. customA white solid was formed
  5. filtrationwhich was collected through suction filtration
  6. washwashed with water
  7. dry with materialdried together with phosphorous pentoxide under vacuum

Sources & evidence

ORD record
ord-8b1b47f0f6c24b938035a2d8ac5f8b86
Source dataset
uspto-grants-2015_04
Patent number
US09012655B2

Reaction notes

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