Trifluoroacetic acid → 1-(Fluoromethyl)cyclopropane-1-sulfonamide

HRID 2361619Notes

Reaction equation

HRID 2361619 reaction equation
[F:1][CH2:2][C:3]1([S:6]([NH:9]C(=O)OC(C)(C)C)(=[O:8])=[O:7])[CH2:5][CH2:4]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][CH2:2][C:3]1([S:6]([NH2:9])(=[O:8])=[O:7])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70978761Tert-butyl 1-fluoromethylcyclopropylsulfonylcarbamate

Product 1

HCID 717427101-(Fluoromethyl)cyclopropane-1-sulfonamideYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (1-(fluoromethyl)cyclopropyl)sulfonylcarbamate (19.8 g, 38.7 mmol) in DCM (100 ml) was added TFA (30 ml, 387 mmol) drop wise at room temperature. The reaction mass was stirred for 2 hr. The reaction mass was evaporated under reduced pressure to get desired compound (6 g, 100%) as off white solid. 1H NMR (400 MHz, CDCl3): δ ppm 4.78-4.66 (d, J=48 Hz, 2H), 2.61 (br, s, 1H), 1.59-1.56 (m, 2H), 1.13-1.10 (m, 2H).

Workup

  1. customThe reaction mass was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d80b4bf4c9e14bf6b441cf4273c82e11
Source dataset
uspto-grants-2014_04
Patent number
US08691757B2

Reaction notes

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