Hydrochloric Acid → Pyroxsulam

HRID 1391842Notes

Reaction equation

HRID 1391842 reaction equation
[NH2:1][C:2]1[N:14]=[C:5]2[N:6]=[C:7]([O:12][CH3:13])[CH:8]=[C:9]([O:10][CH3:11])[N:4]2[N:3]=1.Cl.COC1C=C(OC)N2N=C(N=S(C)C)N=C2N=1.[CH3:33][O:34][C:35]1[C:40]([S:41](Cl)(=[O:43])=[O:42])=[C:39]([C:45]([F:48])([F:47])[F:46])[CH:38]=[CH:37][N:36]=1.N1C=C(C)C=C(C)C=1.Cl>C(#N)C>[CH3:13][O:12][C:7]1[CH:8]=[C:9]([O:10][CH3:11])[N:4]2[N:3]=[C:2]([NH:1][S:41]([C:40]3[C:35]([O:34][CH3:33])=[N:36][CH:37]=[CH:38][C:39]=3[C:45]([F:48])([F:46])[F:47])(=[O:42])=[O:43])[N:14]=[C:5]2[N:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 115653,5-DimethylpyridineHCID 11194901[1,2,4]Triazolo[1,5-a]pyrimidin-2-amine, 5,7-dimethoxy-HCID 185397982-Methoxy-4-(trifluoromethyl)pyridine-3-sulfonyl chlorideHCID 86760623N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-S,S-dimethyl-sulfilimine hydrochloride salt

Product 1

HCID 11571555PyroxsulamYield 82.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Amino-5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidine (9.8 g, 0.050 mol) and N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-S,S-dimethyl-sulfilimine hydrochloride salt (1.5 g, 0.005 mol) solids were combined with 2-methoxy-4-(trifluoromethyl)-pyridine-3-sulfonyl chloride (14 g, 0.051 mol) in acetonitrile (40 mL). 3,5-Lutidine (31 g, 93% technical) was added, and the mixture was stirred at room temperature for 22 hours. The mixture was warmed to 42° C. and treated with 3 N HCl (65 mL), after which the mixture was allowed to cool to room temperature over 1.5 hours. The solids were collected by filtration, washed with a 2:1 v/v solution of water:acetonitrile (20 mL), and dried under vacuum at 60° C. to afford 18 g of product assaying at 94 wt % (78% yield).

Workup

  1. temperatureThe mixture was warmed to 42° C.
  2. temperatureto cool to room temperature over 1.5 hours
  3. filtrationThe solids were collected by filtration
  4. washwashed with a 2:1 v/v solution of water
  5. dry with materialacetonitrile (20 mL), and dried under vacuum at 60° C.

Sources & evidence

ORD record
ord-0b9c78bc135b4afbb31bae5659b4404c
Source dataset
uspto-grants-2008_03
Patent number
US07339058B2

Reaction notes

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