Diisopropylethylamine → N-(sec-butylsulfonyl)-2,4,5-trifluorobenzamide

HRID 2048081Notes

Reaction equation

HRID 2048081 reaction equation
Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)C(C)C)C.[F:22][C:23]1[CH:31]=[C:30]([F:32])[C:29]([F:33])=[CH:28][C:24]=1[C:25]([OH:27])=O.[CH3:34][CH:35]([S:38]([NH2:41])(=[O:40])=[O:39])[CH2:36][CH3:37]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:35]([S:38]([NH:41][C:25](=[O:27])[C:24]1[CH:28]=[C:29]([F:33])[C:30]([F:32])=[CH:31][C:23]=1[F:22])(=[O:40])=[O:39])([CH2:36][CH3:37])[CH3:34]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5211702,4,5-Trifluorobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20482438Butane-2-sulfonamide

Product 1

HCID 58042392N-(sec-butylsulfonyl)-2,4,5-trifluorobenzamideYield 46%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.41 g, 2.1 mmol), 4-dimethylaminopyridine (0.26 g, 2.1 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.9 mL, 4.2 mmol) were added to a solution of 2,4,5-trifluorobenzoic acid (0.25 g, 1.4 mmol) in DCM. After 10 minutes butane-2-sulfonamide (Preparation 29, 0.29 g, 2.1 mmol) was added and the reaction was left at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue purified by preparative HPLC to yield the title compound as a white solid (0.19 g, 31% yield):

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-e254bd20fc5b4f30be7e04f2817fb323
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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