Cyanuric chloride → HCID 59216379, compound

HRID 41906Notes

Reaction equation

HRID 41906 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([CH2:18][C:19]([NH2:21])=O)[CH:14]=3)[C:9]2=[O:22])=[CH:5][CH:4]=1.N1C(Cl)=NC(Cl)=NC=1Cl>C1COCC1.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([CH2:18][C:19]#[N:21])[CH:14]=3)[C:9]2=[O:22])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 7954Cyanuric chlorideHCID 59216414HCID 59216414, compound

Product 1

HCID 59216379HCID 59216379, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The amide (III) (1.3 g, 4 mmole ) was suspended in 5 ml THF and 10 ml DMF. To this mixture was added cyanuric chloride (0.370 g, 2 mmole) and after stirring at room temperature for 0.5 hour, the reaction mixture was partitioned between ethylacetate and brine; the organic layer was washed with 5% sodium bicarbonate, followed by brine and then dried over sodium sulfate. Purification by flash chromatograpy on silica gel column using 75% ethylacetate in hexane as eluent afforded 1.2 g (98% yield) of nitrile (IV).

Workup

  1. customthe reaction mixture was partitioned between ethylacetate and brine
  2. washthe organic layer was washed with 5% sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. customPurification by flash chromatograpy on silica gel column

Sources & evidence

ORD record
ord-032861ef127f431cb04ad84abe418d56
Source dataset
uspto-grants-2013_09
Patent number
US08536166B2

Reaction notes

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