2,4-Dichlorobenzenethiol → HCID 59299320, compound

HRID 2235325Notes

Reaction equation

HRID 2235325 reaction equation
[CH:1]1([N:7]2[CH2:11][C:10]([CH3:13])([CH3:12])[CH:9](OS(C3C=CC(C)=CC=3)(=O)=O)[C:8]2=[O:25])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:26][C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1[SH:34].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[CH:1]1([N:7]2[CH2:11][C:10]([CH3:12])([CH3:13])[CH:9]([S:34][C:28]3[CH:29]=[CH:30][C:31]([Cl:33])=[CH:32][C:27]=3[Cl:26])[C:8]2=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 707302,4-DichlorobenzenethiolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59299352HCID 59299352, compound

Product 1

HCID 59299320HCID 59299320, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Place toluene-4-sulfonic acid 1-cyclohexyl-4,4-dimethyl-2-oxo-pyrrolidin-3-yl ester (0.102 g, 0.28 mmol), 2,4-dichloro-benzenethiol (0.073 ml, 0.56 mmol) and DBU (0.130 ml, 0.84 mmol) in DMF (3 mL). Stir for 5 hours at 50° C. Quench with water and extract with ethyl acetate. Wash the extract brine and dry over magnesium sulfate, filter, and concentrate. Flash chromatography affords 0.030 g (29%) of the title compound: Mass spectrum (apci) m/z=372 (M+H).

Workup

  1. customQuench with water
  2. extractionextract with ethyl acetate
  3. washWash the extract brine
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-5ea9dc57ad6743888e6b7d1ab10ae1ee
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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