Hydrochloric Acid → N-[(5-Phenylthiophen-2-yl)-methylene]-2-methylpropanesulfinamide

HRID 2041239Notes

Reaction equation

HRID 2041239 reaction equation
C1(C2SC(C(N)C)=CC=2)C=CC=CC=1.Cl.O1CCOCC1.[C:22]1([C:28]2[S:32][C:31]([CH:33]([NH:35][S:36]([CH2:38][CH:39]([CH3:41])[CH3:40])=[O:37])C)=[CH:30][CH:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CO>[C:22]1([C:28]2[S:32][C:31]([CH:33]=[N:35][S:36]([CH2:38][CH:39]([CH3:41])[CH3:40])=[O:37])=[CH:30][CH:29]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 30320191-(5-Phenylthiophen-2-yl)ethan-1-amineHCID 66706418N-[1-(5-phenylthiophen-2-yl)ethyl]-2-methylpropanesulfinamide

Product 1

HCID 66706412N-[(5-Phenylthiophen-2-yl)-methylene]-2-methylpropanesulfinamideYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(5-Phenyl-thiophen-2-yl)ethylamine (Isomer 2, Preparation 171) Add 4N hydrogen chloride in dioxane (1.112 mL, 4.449 mmol) to a stirred solution of N-[1-(5-phenylthiophen-2-yl)ethyl]-2-methylpropanesulfinamide (Isomer 2) (684 mg, 2.225 mmol) in methanol (10 mL) at room temperature. Stir for 2 h and remove the solvent in vacuo to obtain a solid that was washed with ethyl ether. Dissolve the solid in DCM and wash with saturated aqueous NaHCO3. Dry the organic phase over Na2SO4, filter and concentrate in vacuo to obtain the desired intermediate (347 mg, 77% yield).

Workup

  1. customremove the solvent in vacuo
  2. customto obtain a solid
  3. washthat was washed with ethyl ether
  4. dissolutionDissolve the solid in DCM
  5. washwash with saturated aqueous NaHCO3
  6. dry with materialDry the organic phase over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-1009c5029a144b02a0e613eca883c4f1
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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