Cyclopropylamine → N-Cyclopropyl 3-bromo-5-trifluoromethylbenzenesulfonamide

HRID 81483Notes

Reaction equation

HRID 81483 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:12](Cl)(=[O:14])=[O:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH:16]1([NH2:19])[CH2:18][CH2:17]1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([S:12]([NH:19][CH:16]2[CH2:18][CH2:17]2)(=[O:14])=[O:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 27786103-Bromo-5-(trifluoromethyl)benzenesulfonyl chloride

Product 1

HCID 26986221N-Cyclopropyl 3-bromo-5-trifluoromethylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Bromo-5-(trifluoromethyl)benzenesulfonyl chloride (0.2 g, 0.62 mmol) is added to a solution of cyclopropylamine (0.09 μl, 1.3 mmol) in DCM (5 ml), and the resulting solution is stirred at room temperature overnight. The reaction mixture is diluted with DCM (2×10 ml), washed with 0.1M HCl (5 ml), sat. aq. NaHCO3 (5 ml), dried (MgSO4) and concentrated in vacuo to yield the title compound. 1H NMR (400 MHz, d6-DMSO) δ 8.37 (1H, s), 8.23 (1H, s), 8.06 (1H, s), 2.21-2.17 (1H, m), 0.55-0.50 (2H, m) 0.40-0.36 (2H, m).

Workup

  1. washwashed with 0.1M HCl (5 ml), sat. aq. NaHCO3 (5 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e87ab9b6205a45d48a44f373460a0fb3
Source dataset
uspto-grants-2014_09
Patent number
US08846687B2

Reaction notes

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