1,2-Dichloroethane → HCID 68183344, compound

HRID 1615523Notes

Reaction equation

HRID 1615523 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[C:14]3[CH:15]=[C:16]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)[S:17][C:13]=3[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.ClCCCl>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]([C:18]4[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=4)[S:17][C:13]=3[CH2:12][CH2:11][CH2:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 111,2-DichloroethaneHCID 681831404-(4-chlorophenyl)-2-pyridin-4-yl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-4-ol

Product 1

HCID 68183344HCID 68183344, compoundYield 91.2%

Conditions

Temperature
60 °C

Procedure

To a solution of 4-(4-chlorophenyl)-2-pyridin-4-yl-5,6,7,8-tetrahydro-4H-cyclohepta thiophene-4-ol (500.0 mg, 1.405 mmol) in 1,2-dichloroethane (6.0 mL, 76 mmol) trifluoroacetic acid (1.082 mL, 14.05 mmol) was added at 0° C., and the resulting brownish solution was heated at 60° C. for 16 hr. The reaction mixture was allowed to cool to rt, the solvent was evaporated, saturated NaHCO3 (5 mL) and ethyl acetate (5 mL) were added, and the mixture was stirred for 30 min, the organic layer was separated, the aqueous layer was extracted with ethyl acetate (3×5 mL), the combined organic layers were dried over MgSO4, filtered, concentrated and the obtained residue was purified by column chromatography (SiO2, elution with 0-100% EA/DCM) to give the title compound as a yellow solid (428.7 mg, 91.2% yield). LCMS: (FA) ES+ , 338/340. 1H NMR (300 MHz, DMSO) E. 8.64 (d, J=6.7 Hz, 2H), 7.92 (d, J=6.6 Hz, 2H), 7.63 (s, 1H), 7.47-7.37 (m, 2H), 7.37-7.21 (m, 2H), 6.49 (t, J=6.5 Hz, 1H), 2.91 (t, J=6.4 Hz, 2H), 2.31-2.07 (m, 4H).

Workup

  1. temperatureto cool to rt
  2. customthe solvent was evaporated
  3. additionsaturated NaHCO3 (5 mL) and ethyl acetate (5 mL) were added
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (3×5 mL)
  6. dry with materialthe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthe obtained residue was purified by column chromatography (SiO2, elution with 0-100% EA/DCM)

Sources & evidence

ORD record
ord-f787106309954786942fc6aa84e97b35
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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