Triethylamine → HCID 90013377, compound

HRID 1776977Notes

Reaction equation

HRID 1776977 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2OS(C)(=O)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[F:26][C:27]([F:36])([F:35])[C:28]1[CH:33]=[CH:32][C:31]([SH:34])=[CH:30][CH:29]=1>ClCCl.C(OCC)(=O)C>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2[S:34][C:31]2[CH:30]=[CH:29][C:28]([C:27]([F:26])([F:35])[F:36])=[CH:33][CH:32]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1366534-(Trifluoromethyl)thiophenolHCID 90019103HCID 90019103, compound

Product 1

HCID 90013377HCID 90013377, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonic acid 7-nitro-1,2,3,4-tetrahydronaphthalen-1-yl ester (1.3 g, 4.8 mmol), was dissolved in a solution of triethylamine (3.35 mL, 24 mmol) and dichloromethane (10 mL). 4-Trifluoromethylbenzenethiol (1.7 g, 9.6 mmol) was then added and the reaction mixture was stirred at room temperature for 6 hours. Next, the reaction mixture was diluted with ethyl acetate and washed with 1N HCl, saturated sodium bicarbonate, and brine. The organic solution was dried (Na2SO4), concentrated, and purified by column chromatography (EtOAc/hexanes) to give 7-nitro-1-(4-trifluoromethylphenylsulfanyl)-1,2,3,4-tetrahydronaphthalene. Yield 1.45 g (86%). LCMS (ESI): calc. C17H14F3NO2S=353; obs. low ionization.

Workup

  1. washwashed with 1N HCl, saturated sodium bicarbonate, and brine
  2. dry with materialThe organic solution was dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by column chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-b510c5f31a2d459391139c19299d7d2e
Source dataset
uspto-grants-2016_02
Patent number
US09266827B2

Reaction notes

Loading…