Trifluoroacetic acid → HCID 118271394, compound

HRID 62631Notes

Reaction equation

HRID 62631 reaction equation
FC(F)(F)C(O)=[O:4].[C:8]1([S:14](/[CH:16]=[C:17](\[C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=2)/[C:18]([F:21])([F:20])[F:19])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:30]([N:37]([CH2:41][Si](C)(C)C)[CH2:38]OC)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1(C)C=CC=CC=1>[CH2:30]([N:37]1[CH2:38][CH:16]([S:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)(=[O:4])=[O:15])[C:17]([C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=2)([C:18]([F:21])([F:19])[F:20])[CH2:41]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine2×HCID 118340468(1E)-2-(3,5-dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfoxide

Product 1

HCID 118271394HCID 118271394, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Trifluoroacetic acid (38 μL, 513 μmol) was added to (1E)-2-(3,5-dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfoxide (4.00 g, 98% purity, 10.3 mmol) in toluene (20 mL). N-Benzyl-1-methoxy-N-[(trimethylsilyl)methyl]methanamine (3.65 g, 15.4 mmol) in toluene (18 mL) was added at room temperature over two hours. After two more hours additional N-Benzyl-1-methoxy-N-[(trimethylsilyl)-methyl]methanamine (0.2 eq.) was added and the reaction left stirring for another hour. The solvents of the reaction mixture were removed and the crude product was taken up in n-heptane. The formed crystals were filtered off. 1-Benzyl-3-(3,5-dichlorophenyl)-4-(phenylsulfinyl)-3-(trifluoromethyl)-pyrrolidinium chloride (4.40 g, >99% purity, 83% yield, E/Z [not assigned]=53/47) was obtained.

Workup

  1. waitthe reaction left
  2. customThe solvents of the reaction mixture were removed
  3. filtrationThe formed crystals were filtered off
  4. customwas obtained

Sources & evidence

ORD record
ord-5d8151d018c746e5b2acf2b6b052a358
Source dataset
uspto-grants-2016_09
Patent number
US09447036B2

Reaction notes

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