Dimethyl Sulfide → Penoxsulam

HRID 1391841Notes

Reaction equation

CSC.ClCl.[NH2:6][C:7]1[N:15]=[C:14]2[N:9]([C:10]([O:18][CH3:19])=[N:11][CH:12]=[C:13]2[O:16][CH3:17])[N:8]=1.N1C=CC=C(C)C=1.[F:27][CH:28]([F:45])[CH2:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[C:32]=1[S:41](Cl)(=[O:43])=[O:42].S(Cl)(Cl)(=O)=O>C(#N)C.O>[F:45][CH:28]([F:27])[CH2:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:38])([F:39])[F:40])[C:32]=1[S:41]([NH:6][C:7]1[N:15]=[C:14]2[N:9]([C:10]([O:18][CH3:19])=[N:11][CH:12]=[C:13]2[O:16][CH3:17])[N:8]=1)(=[O:42])=[O:43]

Participants

Conditions

Temperature: 8 °C

Procedure

A solution of methyl sulfide (0.34 g, 0.0055 mol) in acetonitrile (40 mL) was cooled to −25° C. To the cold solution was added a cold, freshly prepared 17 wt % solution of chlorine in acetonitrile (2.4 g, 0.0057 mol) over several minutes. While still cold, 1.1 g of 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine (1.1 g, 0.0056 mol) and 3-picoline (0.95 g, 0.010 mol) were added. The mixture was allowed to warm to 8° C. 3-Picoline (48 g, 0.52 mol), 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine (18.4 g, 0.094 mol), and 2-(2,2-difluoroethoxy)-6-(trifluoromethyl)benzenesulfonyl chloride (32.5 g, 0.10 mol) were added in order to the reactor. The mixture was stirred and heated at ˜40° C. for 24 hours, then at room temperature for 48 hours. The reaction slurry was converted into a solution by the addition of acetonitrile (600 mL) and water (100 mL). The solution was assayed for product by HPLC and determined to contain 42 g (86% yield, in situ, from sulfonyl chloride).

Workup

temperatureheated at ˜40° C. for 24 hours

Sources & evidence

ORD record: ord-facb76c3fef44081853c2bee0838a965
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07339058B2

Reaction notes

Loading…