Potassium Carbonate → 3-chloro-2-methyl-N-(2-methyl-1,3-benzothiazol-5-yl)benzenesulfonamide

HRID 970036Notes

Reaction equation

HRID 970036 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].BrC[C:21]1[CH:22]=[CH:23][C:24]2[S:28][C:27]([CH3:29])=[N:26][C:25]=2[CH:30]=1>CC#N>[CH3:12][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[S:8]([NH:11][C:21]1[CH:22]=[CH:23][C:24]2[S:28][C:27]([CH3:29])=[N:26][C:25]=2[CH:30]=1)(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 8172313-Chloro-2-methylbenzenesulfonamideHCID 211907575-Bromomethyl-2-methylbenzothiazole

Product 1

HCID 69188703-chloro-2-methyl-N-(2-methyl-1,3-benzothiazol-5-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-chloro-2-methylbenzenesulphonamide (103 mg, 0.5 mmol) in CH3CN was added potassium carbonate (100 mg), followed 5-bromomethyl-2-methylbenzothiazole (121 mg, 0.5 mmol). The mixture was refluxed under N2 for 6 h, partitioned between ethyl acetate and water. The organic phase was washed brine, dried over sodium sulphate and concentrated in vacuo to give a yellow residue, which was separated with flash chromatography (ethyl acetate/DCM, gradient elution). STX1029 was obtained as white solid. TLC single spot at Rf 0.55 (10% EtOAc/DCM); HPLC purity >99% (tR 2.0 min in 10% water-methanol); 1HNMR (270 MHz, CDCl3) δ7.89 (1H, d, J=7.9 Hz, ArH), 7.66 (1H, d, J=7.9 Hz, ArH), 7.65 (1H, d, J=1.3 Hz, ArH), 7.49 (1H, d, J=7.9 Hz, ArH), 7.17 (1H, t, J=7.9 Hz, ArH), 7.13 (1H, dd, J=7.9, 1.5 Hz, ArH), 5.35 (1H, t, J=5.9 Hz, NH), 4.24 (2H, d, J=5.9 Hz, CH2), 2.79 (3H, s, CH3), 2.62 (3H, s, CH3); APCI-MS 367 (MH)+; FAB-HRMS calcd for C16H16ClN2O2S2 (MH+) 367.0342, found 367.0330.

Workup

  1. temperatureThe mixture was refluxed under N2 for 6 h
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase was washed brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customto give a yellow residue, which
  7. customwas separated with flash chromatography (ethyl acetate/DCM, gradient elution)

Sources & evidence

ORD record
ord-9b5dd938bf0b406c86f403cdecbdc66d
Source dataset
uspto-grants-2007_12
Patent number
US07309715B2

Reaction notes

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