1,2-Ethanedithiol → HCID 86615015, compound

HRID 732554Notes

Reaction equation

HRID 732554 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:16]=[C:15]([C:17]([C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)=O)[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.[CH2:25]([SH:28])[CH2:26][SH:27].B(F)(F)F.CCCCOCCCC>ClCCl>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:16]=[C:15]([C:17]2([C:19]3[O:20][CH:21]=[CH:22][CH:23]=3)[S:28][CH2:25][CH2:26][S:27]2)[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1

Participants

5

Reactant 3

HCID 109021,2-EthanedithiolHCID 68970Boron, trifluoro[1,1'-oxybis[butane]]-, (T-4)-HCID 68816228HCID 68816228, compound

Product 1

HCID 86615015HCID 86615015, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolve 5-(furan-2-carbonyl)-N-methyl-N-propyl-isophthalamic acid methyl ester (290 mg, 0.88 mmol) in dichloromethane (2 mL). Cool to 0° C., add a solution of ethane-1,2-dithiol (0.22 mL, 2.2 mmol) and then add a solution of boron trifluoride dibutyl etherate (0.66 mL, 5.2 mmol) in dichloromethane (5 mL). Warm the mixture to room temperature and stir overnight. Quench with water and dilute with dichloromethane. Wash the organic layer by saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 0:100 to 30:70 ethyl acetate:hexanes) to give the title compound (38%).

Workup

  1. temperatureWarm the mixture to room temperature
  2. customQuench with water
  3. additiondilute with dichloromethane
  4. washWash the organic layer by saturated aqueous sodium chloride
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with 0:100 to 30:70 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-8cc3457b1cb342b0a80fcd8b68f3ddaa
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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