Triethylamine → N-cyclopropyl-3-trifluoromethylbenzylsulfonamide

HRID 1762300Notes

Reaction equation

HRID 1762300 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C(N(CC)CC)C.[F:12][C:13]([F:26])([F:25])[C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=1)[CH2:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH:1]1([NH:4][S:18]([CH2:17][C:16]2[CH:22]=[CH:23][CH:24]=[C:14]([C:13]([F:12])([F:25])[F:26])[CH:15]=2)(=[O:20])=[O:19])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 27946463-(Trifluoromethyl)phenylmethanesulfonyl chloride

Product 1

HCID 15615994N-cyclopropyl-3-trifluoromethylbenzylsulfonamideYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In this example 5.3 g of cyclopropylamine were mixed with 9.4 g of triethylamine and then added drop-wise to a solution containing 20 g of 3-trifluoromethylbenzylsulfonyl chloride in methylene chloride at 0° C. The resulting reaction mixture was stirred at room temperature (i.e., about 20°-25° C.) for 3 hours. The reaction mixture was then washed with saturated aqueous ammonium chloride and then with aqueous 1 wt. % hydrochloric acid until it was neutral. The organic layer was then separated, washed twice with 50 ml of aqueous saturated sodium chloride solution, dried over magnesium sulfate and then evaporated to dryness affording 20 g of N-cyclopropyl-3-trifluoromethylbenzylsulfonamide.

Workup

  1. additionadded drop-wise to a solution
  2. customThe resulting reaction mixture
  3. washThe reaction mixture was then washed with saturated aqueous ammonium chloride
  4. customThe organic layer was then separated
  5. washwashed twice with 50 ml of aqueous saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-e9d694cef89f439f969bfdde7f6e6345
Source dataset
uspto-grants-1989_05
Patent number
US04831179

Reaction notes

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