2-Pyridinesulfonamide, 3-iodo- → HCID 19044125, compound

HRID 260631Notes

Reaction equation

HRID 260631 reaction equation
C[Al](C)C.[I:5][C:6]1[C:7]([S:12]([NH2:15])(=[O:14])=[O:13])=[N:8][CH:9]=[CH:10][CH:11]=1.[CH3:16][O:17][C:18]1[N:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20]([NH:26][C:27](=O)[O:28]C)[N:19]=1>C1(C)C=CC=CC=1.ClCCl>[CH3:25][O:24][C:22]1[N:23]=[C:18]([O:17][CH3:16])[N:19]=[C:20]([NH:26][C:27](=[O:28])[NH:15][S:12]([C:7]2[C:6]([I:5])=[CH:11][CH:10]=[CH:9][N:8]=2)(=[O:13])=[O:14])[N:21]=1

Participants

6

Reactant 3

HCID 12144982-Pyridinesulfonamide, 3-iodo-HCID 12803256Methyl (4,6-dimethoxy-1,3,5-triazin-2-yl)carbamateHCID 16682925Trimethylaluminum

Product 1

HCID 19044125HCID 19044125, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

9.0 ml (18 mmol) of a 2M solution of trimethylaluminum in toluene are added dropwise at room temperature to 4.3 g (15 mmol) of 3-iodo-2-pyridinesulfonamide in 150 ml of dichloromethane. After evolution of gas has ceased, 3.85 [lacuna] (18 mmol) of methyl 4,6-dimethoxy-1,3,5-triazin-2-yl-carbamate in 20 ml of dichloromethane is added dropwise and the resulting solution is refluxed for 24 hours. The mixture is cooled and poured into 150 ml of ice-cold 1N hydrochloric acid. The organic phase is separated off and the aqueous phase is extracted 2x using dichloromethane. The organic phase is dried and evaporated. After triturating the crude product with diethyl ether, 3,1 g (44% of theory) of 3-(4,6-dimethoxy-1,3,5-triazin-2-yl)-1-(3-iodo-2-pyridylsulfonyl)urea of melting point 155° C. (dec.) are obtained.

Workup

  1. temperaturethe resulting solution is refluxed for 24 hours
  2. temperatureThe mixture is cooled
  3. customThe organic phase is separated off
  4. extractionthe aqueous phase is extracted 2x
  5. customThe organic phase is dried
  6. customevaporated
  7. customAfter triturating the crude product with diethyl ether, 3,1 g (44% of theory) of 3-(4,6-dimethoxy-1,3,5-triazin-2-yl)-1-(3-iodo-2-pyridylsulfonyl)urea of melting point 155° C. (dec.)
  8. customare obtained

Sources & evidence

ORD record
ord-7f15fb744ce4426ea96d1f1da9b10577
Source dataset
uspto-grants-1996_06
Patent number
US05529976

Reaction notes

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