Potassium Carbonate → 4-(4,4-Difluorobut-3-enylthio)-1,2,3-benzotriazine

HRID 725013Notes

Reaction equation

HRID 725013 reaction equation
SC1C2C=CC=CC=2N=NN=1.CS(OCCCC(Br)(F)F)(=O)=O.C(=O)([O-])[O-].[K+].[K+].Br[C:31]([F:47])([F:46])[CH2:32][CH2:33][CH2:34][S:35][C:36]1[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[N:39]=[N:38][N:37]=1>CC(C)=O.CCCCCC.C(OCC)(=O)C>[F:47][C:31]([F:46])=[CH:32][CH2:33][CH2:34][S:35][C:36]1[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[N:39]=[N:38][N:37]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 218503674-(4-Bromo-4,4-difluorobutylthio)-1,2,3-benzotriazineHCID 218503894-Bromo-4,4-difluorobutyl methanesulfonateHCID 178527983HCID 178527983, compound

Product 1

HCID 218503794-(4,4-Difluorobut-3-enylthio)-1,2,3-benzotriazine

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Step 1 (1 g), 4-bromo-4,4-difluorobutyl methanesulfonate (1.65 g) and potassium carbonate (0.852 g) were stirred together in acetone (30 cm3) at ambient temperature for 36 hours. Inorganic solids were removed by filtration and the filtrate evaporated under reduced pressure to give a brown oil. Chromatography on silica gel using 1:4 ethyl acetate:hexane as eluant gave two yellow oils (ea 0.5 g). The first-eluted oil was identified as N-alkylated material and the second was the desired S-alkyated intermediate 4-(4-bromo-4,4-difluorobutylthio)-1,2,3-benzotriazine. 1H NMR: δ 2.18-2.31 (2H,m); 2.58-2.71 (2H,m); 3.63(2H,t); 7.95(1H,t); 8.09(2H,m); 8.40(1H,d).

Workup

  1. customInorganic solids were removed by filtration
  2. customthe filtrate evaporated under reduced pressure
  3. customto give a brown oil

Sources & evidence

ORD record
ord-e4cf36993782409e93aa3b7a034456f9
Source dataset
uspto-grants-1998_01
Patent number
US05705516

Reaction notes

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