Hydrochloric Acid → Hydrochloric Acid

HRID 1518204Notes

Reaction equation

HRID 1518204 reaction equation
[F:1][C:2]([F:25])([F:24])[O:3][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.B.CSC.[ClH:30]>O1CCCC1.C(O)C>[F:25][C:2]([F:1])([F:24])[O:3][C:4]1[CH:5]=[CH:6][C:7]([S:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH2:23])=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:8][CH:9]=1.[ClH:30]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 12423031(Dimethyl sulfide)trihydroboronHCID 67132909HCID 67132909, compound

Product 2

HCID 313Hydrochloric AcidYield 84.7%HCID 67132620HCID 67132620, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[4-(4-trifluoromethoxy-benzenesulfonylmethyl)-phenyl]-acetamide (1.36 g, 3.64 mmol) in tetrahydrofuran (30 ml) was refluxed and a solution of borane-dimethylsulfid complex (2M in tetrahydrofuran, 9.11 mmol) was added. The mixture was refluxed for 2 h. The mixture was allowed to come to room temperature and was adjusted to pH=1 using a solution of HCl in ethanol (2M). After stirring the mixture for 15 min the solvents were evaporated under reduced pressure. 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-trifluoromethoxy-benzenesulfonylmethyl)-phenyl]-ethylamine×HCl (1.22 g, 84.7%).

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customto come to room temperature
  3. customwere evaporated under reduced pressure
  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-50141ef6dabc4628b7ff1d5153e6edf7
Source dataset
uspto-grants-2012_07
Patent number
US08232426B2

Reaction notes

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