Hydrochloric Acid → Hydrochloric Acid

HRID 1518203Notes

Reaction equation

HRID 1518203 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([NH2:23])=O)=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].B.CSC.[ClH:28]>O1CCCC1.C(O)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][NH2:23])=[CH:18][CH:19]=2)(=[O:12])=[O:11])=[CH:8][CH:9]=1)([CH3:3])[CH3:2].[ClH:28]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 12423031(Dimethyl sulfide)trihydroboronHCID 67132847HCID 67132847, compound

Product 2

HCID 313Hydrochloric AcidYield 92.6%HCID 67132865HCID 67132865, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[4-(4-isopropyl-benzenesulfonylmethyl)-phenyl]-acetamide (1.37 g, 4.13 mmol) in tetrahydrofuran (30 ml) was refluxed and then a solution of borane-dimethylsulfid complex (2M in tetrahydrofuran, 10.33 mmol) was added. The mixture was refluxed for 2 h. The mixture was allowed to cool down to room temperature and adjusted to pH=1 with a solution of HCl in ethanol (2M). After stirring the mixture for 15 min the solvents were evaporated under reduce pressure. Diethyl ether was added to residue. A slurry of the resulting white powder in diethyl ether was stirred for 15 min. The remaining solid was collected, washed with diethyl ether, and dried in a vacuum oven to give white crystals of 2-[4-(4-isopropyl-benzenesulfonylmethyl)-phenyl]-ethylamine×HCl (1.36 g, 92.6%).

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customwere evaporated
  3. additionDiethyl ether was added to residue
  4. stirringA slurry of the resulting white powder in diethyl ether was stirred for 15 min
  5. customThe remaining solid was collected
  6. washwashed with diethyl ether
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-b24efabe748a40c6a1fd52db715df404
Source dataset
uspto-grants-2012_07
Patent number
US08232426B2

Reaction notes

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