Cyanuric chloride → HCID 59656634, compound

HRID 2054909Notes

Reaction equation

HRID 2054909 reaction equation
[NH2:1][C:2]1[C:3]2[C:13]([O:14][CH:15]3[CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=[C:10]([C:19]([NH2:21])=O)[C:4]=2[S:5][C:6]=1[C:7]([NH2:9])=[O:8].N1C(Cl)=NC(Cl)=NC=1Cl>CN(C=O)C.O>[NH2:1][C:2]1[C:3]2[C:13]([O:14][CH:15]3[CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=[C:10]([C:19]#[N:21])[C:4]=2[S:5][C:6]=1[C:7]([NH2:9])=[O:8]

Participants

5

Reactant 2

HCID 7954Cyanuric chlorideHCID 11301190Benzo[b]thiophene-2,7-dicarboxamide, 3-amino-4-(cyclobutyloxy)-

Product 1

HCID 59656634HCID 59656634, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of the above amide (200 mg, 0.655 mmol) in DMF (3 mL) was added cyanuric chloride (60 mg, 0.325 mmol). The reaction was stirred at room temperature for 1 h. The mixture was slowly diluted with water (10 mL) and extracted with dichloromethane. The aqueous phase was allowed to stand for two weeks then the precipitate formed was collected by filtration, rinsed with MeOH and dried in vacuo to give the title compound (93.5 mg, 0.315 mmol, 48.1%).

Workup

  1. extractionextracted with dichloromethane
  2. waitto stand for two weeks
  3. customthe precipitate formed
  4. filtrationwas collected by filtration
  5. washrinsed with MeOH
  6. customdried in vacuo

Sources & evidence

ORD record
ord-f01a7c06250f46ffaf6f80cb87feb27d
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

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