4-Fluorobenzenesulfonyl chloride → HCID 22713308, compound

HRID 1278745Notes

Reaction equation

HRID 1278745 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:5][CH2:4]1.C(N(C(C)C)CC)(C)C.[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>C(Cl)Cl>[CH:3]1([CH2:2][NH:1][S:22]([C:19]2[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=2)(=[O:24])=[O:23])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 75646CyclopropanemethanamineHCID 81531Diisopropylethylamine

Product 1

HCID 22713308HCID 22713308, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2 mL (23 mmol) of aminomethyl cyclopropane in 25 mL methylene chloride was added 4.8 mL (28 mmol) of diisopropylethyl amine. After 10 minutes of stirring, 4.49 g (23 mmol) of 4-fluorobenzene sulfonyl chloride was added and the mixture was allowed to stir for 4 hours. The reaction mixture was quenched with water and the organic layer was washed twice with 1N HCl, twice with water, dried over magnesium sulfate and then concentrated in vacuo. Then the solid was dried under vacuum to give 4.65 g of the title compounds as an off white solid; 1H NMR (CDCl3) δ 0.08-0.13 (m, 2H), 0.45-0.51 (m, 2H), 0.83-0.94 (m, 1H), 2.86 (t, J=6.9 Hz, 2H), 4.66-4.71 (m, 1H), 7.12-7.23 (m, 2H); MS (ES) m/z 218.23 (MH+); HRMS for C10H12FNO2S: 218.0637.

Workup

  1. stirringto stir for 4 hours
  2. customThe reaction mixture was quenched with water
  3. washthe organic layer was washed twice with 1N HCl, twice with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThen the solid was dried under vacuum

Sources & evidence

ORD record
ord-2f0f3db6eaf649d6941c3c4c244cd415
Source dataset
uspto-grants-2002_09
Patent number
US06444685B1

Reaction notes

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