Triethylamine → N-(5-Bromo-benzothiazol-2-ylmethyl)-methanesulfonamide

HRID 1487467Notes

Reaction equation

HRID 1487467 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][NH2:11])=[N:7][C:6]=2[CH:12]=1.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][NH:11][S:21]([CH3:20])(=[O:23])=[O:22])=[N:7][C:6]=2[CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 433062172-Benzothiazolemethanamine, 5-bromo-

Product 1

HCID 86695423N-(5-Bromo-benzothiazol-2-ylmethyl)-methanesulfonamideYield 43.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of C-(5-Bromo-benzothiazol-2-yl)-methylamine (0.780 g, 3.209 mmol) in CH2Cl2 (12 mL) is added triethylamine (1.2 mL, 8.024 mmol). To above solution is added drop wise methane sulfonyl chloride (0.5 mL, 6.419 mmol) at 0° C. then stirred at room temperature for 3 hours. The reaction mixture is concentrated in vacuo and the crude material is diluted with water and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, concentrated and purified by combiflash using 50% ethyl acetate in hexane as an eluent to afford the title compound (0.45 g). 1HNMR (400 MHz, DMSO-d6) δ: 3.03 (s, 3H), 4.60 (d, J=5.72 Hz, 2H), 7.64-7.67 (dd, J1=1.88 Hz, J2=8.72 Hz, 1H), 7.88 (d, J=8.68 Hz, 1H), 8.21 (t, J=6 Hz, 1H), 8.40 (d, J=1.88 Hz, 1H). LC-MS (m/z): [M−H]=320.8.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. additionthe crude material is diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by combiflash

Sources & evidence

ORD record
ord-3d13006c1c6343259db7574882fec1b6
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Reaction notes

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