Hydrochloric Acid → 4-[[(1-Propyl-1H-imidazol-5-yl)methyl]sulfinyl]benzenamine

HRID 402297Notes

Reaction equation

HRID 402297 reaction equation
O.C1(C)C=CC(C([C@](C(O)=O)(O)[C@](C(C2C=CC(C)=CC=2)=O)(O)C(O)=O)=[O:9])=CC=1.[CH2:30]([N:33]1[C:37]([CH2:38][S:39][C:40]2[CH:45]=[CH:44][C:43]([NH2:46])=[CH:42][CH:41]=2)=[CH:36][N:35]=[CH:34]1)[CH2:31][CH3:32].Cl>C(OCC)(=O)C>[CH2:30]([N:33]1[C:37]([CH2:38][S:39]([C:40]2[CH:41]=[CH:42][C:43]([NH2:46])=[CH:44][CH:45]=2)=[O:9])=[CH:36][N:35]=[CH:34]1)[CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131726867HCID 131726867, compound

Product 1

HCID 229386104-[[(1-Propyl-1H-imidazol-5-yl)methyl]sulfinyl]benzenamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To (−)-4-{[(1-propyl-1H-imidazol-5-yl)methyl]sulfenyl}phenylamine di-p-toluoyl-D-tartarate monohydrate (5 g) were added 1N hydrochloric acid (25 ml) and ethyl acetate (15 ml) to effect reverse extraction. To the aqueous layer was added aqueous 25% potassium carbonate solution (25 ml)(pH 9) and the mixture was extracted with 25 ml of ethyl acetate —IPA (4:1) three times. The organic layer was washed with saturated brine (25 ml) and dried with magnesium sulfate. The solvent was distilled off to give (−)-4-{[(1-propyl-1H-imidazol-5-yl)methyl]sulfinyl}-phenylamine.

Workup

  1. extractionextraction
  2. additionTo the aqueous layer was added aqueous 25% potassium carbonate solution (25 ml)(pH 9)
  3. extractionthe mixture was extracted with 25 ml of ethyl acetate —IPA (4:1) three times
  4. washThe organic layer was washed with saturated brine (25 ml)
  5. dry with materialdried with magnesium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-0fb473e887624d6a9ba2db705c1c35ce
Source dataset
uspto-grants-2014_06
Patent number
US08741943B2

Reaction notes

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