Benzenesulfonyl chloride → HCID 59859943, compound

HRID 2174950Notes

Reaction equation

HRID 2174950 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:11]1([S:17](Cl)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][S:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:19])=[O:18])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 447548695-Bromo-2-methoxypyridin-3-amine

Product 1

HCID 59859943HCID 59859943, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-bromo-2-methoxypyridin-3-amine (1.231 mmol) was dissolved in pyridine (3 ml) at 0° C. Benzene sulfonyl chloride (1.847 mmol) was added drop wise and the reaction mixture was stirred at RT for 2 h. The reaction mixture was evaporated to dryness and the residue was dissolved in ethyl acetate (100 mL). The ethyl acetate layer was washed with water, separated and dried over sodium sulfate. The organic layer was evaporated to dryness. The crude material obtained was purified by (silica column, EtOAc/Hexane as eluent) to obtain the title compound. 1HNMR (300 MHz, DMSO-d6): δ 10.16 (s, 1H), 8.05 (d, J=2.4 Hz, 1H), 7.77 (m, 2H), 7.68 (d, J=2.4 Hz, 1H), 7.64 (m, 1H), 7.55 (m, 1H), 3.61 (s, 3H); MS (m/z): 343 (M)+.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  3. washThe ethyl acetate layer was washed with water
  4. customseparated
  5. dry with materialdried over sodium sulfate
  6. customThe organic layer was evaporated to dryness
  7. customThe crude material obtained
  8. customwas purified by (silica column, EtOAc/Hexane as eluent)

Sources & evidence

ORD record
ord-7db1d4af3a2049ada70bec6008e9cbe7
Source dataset
uspto-grants-2015_06
Patent number
US09062046B2

Reaction notes

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