Hydrochloric Acid → Penoxsulam

HRID 1391844Notes

Reaction equation

HRID 1391844 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[N:4]([C:5]([O:13][CH3:14])=[N:6][CH:7]=[C:8]2[O:11][CH3:12])[N:3]=1.[F:15][CH:16]([F:33])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[C:20]=1[S:29](Cl)(=[O:31])=[O:30].N1C=C(C)C=C(C)C=1.Cl>C(#N)C.CS(C)=O>[F:33][CH:16]([F:15])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[C:20]=1[S:29]([NH:1][C:2]1[N:10]=[C:9]2[N:4]([C:5]([O:13][CH3:14])=[N:6][CH:7]=[C:8]2[O:11][CH3:12])[N:3]=1)(=[O:30])=[O:31]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 115653,5-DimethylpyridineHCID 114468885,8-Dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amineHCID 160503082-(2,2-Difluoroethoxy)-6-(trifluoromethyl)benzene-1-sulfonyl chloride

Product 1

HCID 11784975PenoxsulamYield 91%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideCatalystHCID 6342AcetonitrileSolvent

Procedure

2-Amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine (19.5 g, 0.10 mol) and 2-(2,2-difluoro-ethoxy)-6-(trifluoromethyl)benzenesulfonyl chloride (32.5 g, 0.10 mol) were combined in acetonitrile (45 mL) and 3,5-lutidine (17 g, 93% technical, ˜0.16 mol) at room temperature. After 10 minutes, DMSO (0.20 g, 0.0026 mol) was added and the reaction slurry was stirred at room temperature for 24 hours. The mixture was then warmed to 48° C. and acidified by the addition of 2 N HCl (100 mL) over 30 minutes, during which the temperature was allowed to fall to ˜38° C. The warm mixture was stirred for one hour, then cooled to 10° C. The precipitated solids were filtered, washed with water (30 mL), washed with methanol (75 mL), and dried under vacuum to afford 44 g of product as a light tan solid assaying at 98 wt % (89% yield).

Workup

  1. customat room temperature
  2. temperatureThe mixture was then warmed to 48° C.
  3. customto fall to ˜38° C
  4. stirringThe warm mixture was stirred for one hour
  5. temperaturecooled to 10° C
  6. filtrationThe precipitated solids were filtered
  7. washwashed with water (30 mL)
  8. washwashed with methanol (75 mL)
  9. customdried under vacuum

Sources & evidence

ORD record
ord-c3f0c60a311d4c598e23d9d4515a6d1b
Source dataset
uspto-grants-2008_03
Patent number
US07339058B2

Reaction notes

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