Sulfamide → 4H-3-Thia-2,4,5-triaza-phenanthrene 3,3-dioxide

HRID 513686Notes

Reaction equation

HRID 513686 reaction equation
[NH2:1][C:2]1[C:3]([CH:12]=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[S:14](N)([NH2:17])(=[O:16])=[O:15]>N1C=CC=CC=1>[CH:12]1[C:3]2[CH:4]=[CH:5][C:6]3[C:11](=[N:10][CH:9]=[CH:8][CH:7]=3)[C:2]=2[NH:1][S:14](=[O:16])(=[O:15])[N:17]=1

Participants

4

Reactant 2

HCID 82267SulfamideHCID 110520988-Aminoquinoline-7-carboxaldehyde

Product 1

HCID 681833864H-3-Thia-2,4,5-triaza-phenanthrene 3,3-dioxideYield 82.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8-Amino-quinoline-7-carbaldehyde 404 (100 mg, 0.58 mmol) and sulfamide (558 mg, 5.81 mmol) in pyridine (2 ml) was heated in a microwave at 140° C. for 2 h. After cooling, the mixture was concentrated in vacuo. The crude residue was dissolved in DCM and neutralised with citric acid. The resulting precipitate was collected by filtration and dried to give the title compound (111 mg, 82%) which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. dissolutionThe crude residue was dissolved in DCM and neutralised with citric acid
  4. filtrationThe resulting precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-c2667734589c408597609779491dae32
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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