Propane-2-sulfonamide → HCID 19912223, compound

HRID 1090990Notes

Reaction equation

HRID 1090990 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([F:18])[C:15]([N:19]2[C:23](=[O:24])[N:22]([CH:25]([F:27])[F:26])[C:21]([CH3:28])=[N:20]2)=[CH:14][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](Cl)=[O:12])=[CH:7][CH:6]=1.[S:29]([CH:33]([CH3:35])[CH3:34])(=[O:32])(=[O:31])[NH2:30]>C(Cl)Cl>[CH3:34][CH:33]([S:29]([NH:30][C:11]([C:8]1[CH:9]=[CH:10][C:5]([O:4][C:3]2[CH:14]=[C:15]([N:19]3[C:23](=[O:24])[N:22]([CH:25]([F:26])[F:27])[C:21]([CH3:28])=[N:20]3)[C:16]([F:18])=[CH:17][C:2]=2[Cl:1])=[CH:6][CH:7]=1)=[O:12])(=[O:32])=[O:31])[CH3:35]

Participants

4

Reactant 2

HCID 3549191Propane-2-sulfonamideHCID 54327510HCID 54327510, compound

Product 1

HCID 19912223HCID 19912223, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
195 °C

Procedure

A stirred mixture of 0.59 g (0.0014 mole) of 4-[2-chloro-4-fluoro-5-(4-difluoromethyl -4,5-dihydro-3-methyl-5-oxo-1H-1,2,4 triazol-1-yl)phenoxy]phenyl-carboxylic acid chloride and 0.17 g (0.0014 mole) of 2-sulfamylpropane was heated at 195° C. for approximately 15 minutes. The mixture was cooled and 2 mL of methylene chloride was added. The mixture was allowed to stand at room temperature for approximately 18 hours. A brown solid formed, was collected and triturated with petroleum ether. Recovery of the solid by filtration gave 0.58 g of N-(1-methylethyl)sulfonyl-4-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]phenylcarboxamide as a solid, m.p. 185°-187° C., Compound 130 of Table 1.

Workup

  1. temperatureThe mixture was cooled
  2. customA brown solid formed
  3. customwas collected
  4. customtriturated with petroleum ether
  5. filtrationRecovery of the solid by filtration

Sources & evidence

ORD record
ord-055385d18bc64400bb9b10c357d36548
Source dataset
uspto-grants-1992_01
Patent number
US05084085

Reaction notes

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