Hydrochloric Acid → (R,E)-N-(4-Cyano-1-phenylbut-3-en-2-yl)-2-(trifluoromethoxy)benzenesulfonamide

HRID 1429408Notes

Reaction equation

HRID 1429408 reaction equation
[NH2:1][C@H:2]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)/[CH:3]=[CH:4]/[C:5]#[N:6].[F:14][C:15]([F:28])([F:27])[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23](Cl)(=[O:25])=[O:24].Cl>C(Cl)Cl>[C:5](/[CH:4]=[CH:3]/[C@H:2]([NH:1][S:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[O:16][C:15]([F:14])([F:27])[F:28])(=[O:25])=[O:24])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)#[N:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27772152-(Trifluoromethoxy)benzene-1-sulfonyl chlorideHCID 68233458(R,E)-4-Amino-5-phenylpent-2-enenitrile

Product 1

HCID 71269687(R,E)-N-(4-Cyano-1-phenylbut-3-en-2-yl)-2-(trifluoromethoxy)benzenesulfonamideYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 31f (2.5 g, 14.5 mmol) in DCM (100 mL) was added 2-(trifluoromethoxy)benzene-1-sulfonyl chloride (4.2 g, 16.0 mmol) and TEA (4.4 g, 3.5 mmol). The mixture was stirred at rt for 12 h, then DCM (50 mL) and 2N HCl (20 mL) were added to the mixture. The organic layer was separated and washed with brine and dried over anhydrous Na2SO4. After filtration, the filtrate was evaporated and the residue was purified by CC (hexane/EA=5:1) to give compound 31g (4.2 g, 74% yield).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationAfter filtration
  5. customthe filtrate was evaporated
  6. customthe residue was purified by CC (hexane/EA=5:1)

Sources & evidence

ORD record
ord-2880d47c1c314bc3811bd7ee37b82585
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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