Hydrogen Bromide → HCID 69694015, compound

HRID 1071572Notes

Reaction equation

HRID 1071572 reaction equation
[N:1]1[S:5][N:4]=[C:3]2[CH:6]=[C:7]([C:10](=[O:19])[CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=3)[CH:8]=[CH:9][C:2]=12.Br.C(=O)(O)[O-:22].[Na+]>CS(C)=O.O>[N:1]1[S:5][N:4]=[C:3]2[CH:6]=[C:7]([C:10](=[O:19])[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=3)=[O:22])[CH:8]=[CH:9][C:2]=12

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 696935641-(2,1,3-Benzothiadiazol-5-yl)-2-(6-methyl-2-pyridinyl)ethanone

Product 1

HCID 69694015HCID 69694015, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

1-Benzo[1,2,5]thiadiazol-5-yl -2-(6-methyl-pyridin-2-yl)-ethanone (5.88 g, 21.8 mmol) was dissolved in dimethyl sulfoxide (50 ml) heated to 60° C. Hydrogen bromide (7.1 ml of a 48% solution in water) was added dropwise and the reaction stirred for 3 hours at 60° C. The cooled reaction was poured into water (100 ml) and the pH adjusted to pH 8 with saturated sodium bicarbonate solution. The organic product was extracted into ethyl acetate (3×100 ml), dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure (5.19 g, 84%); 1H NMR (250 MHz, CDCl3) δ: 2.47 (3H, s), 7.40 (1H, d), 7.85 (1H, t), 8.06 (1H, d), 8.15 (1H, d), 8.28 (1H, d), 8.45 (1H, s); m/z(API) 284 (M+H+, 100%).

Workup

  1. customThe cooled reaction
  2. extractionThe organic product was extracted into ethyl acetate (3×100 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated to dryness under reduced pressure (5.19 g, 84%)

Sources & evidence

ORD record
ord-772f35da516c42b0aea25cb4f631559f
Source dataset
uspto-grants-2005_06
Patent number
US06906089B2

Reaction notes

Loading…