1,2-Ethanedithiol → HCID 178441433, compound

HRID 1457782Notes

Reaction equation

HRID 1457782 reaction equation
[CH2:1]([C:5]1[N:21]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]3[N:39](C(OCC)C)[N:38]=[N:37][N:36]=3)=[CH:25][CH:24]=2)[C:8]2=[N:9][C:10]([CH:19]=O)=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:12]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4].[CH2:45]([SH:48])[CH2:46][SH:47].C([O-])(O)=O.[Na+]>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([C:5]1[N:21]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]3[NH:36][N:37]=[N:38][N:39]=3)=[CH:25][CH:24]=2)[C:8]2=[N:9][C:10]([CH:19]3[S:48][CH2:45][CH2:46][S:47]3)=[C:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:12]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 109021,2-EthanedithiolHCID 516892Sodium BicarbonateHCID 22100380HCID 22100380, compound

Product 1

HCID 178441433HCID 178441433, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

0.1 g(0.000169 mole) of the aldehyde compound obtained in step 11 of Example 1 and 0.024 g(0.00025 mole) of 1,2-ethanedithiol were dissolved in 5 ml of benzene and to the resulting solution was added 0.01 mg of p-toluenesulfonic acid. The resultant was refluxed for 6 hours, neutralized with aqueous NaHCO3 solution and extracted with ethyl acetate(5 ml×3). The organic layer was dried over Na2SO4, concentrated under reduced pressure and evaporated under reduced pressure (1 mmHg, 80° C.) for 5 hours to remove the residual 1,2-ethanedithiol. The resultant was recrystallized from hexane-methylene chloride to obtain 80 mg of the title compound(yield 84%).

Workup

  1. temperatureThe resultant was refluxed for 6 hours
  2. extractionextracted with ethyl acetate(5 ml×3)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customevaporated under reduced pressure (1 mmHg, 80° C.) for 5 hours
  6. customto remove the residual 1,2-ethanedithiol
  7. customThe resultant was recrystallized from hexane-methylene chloride

Sources & evidence

ORD record
ord-00abc6bf9dcd44b19c3cdd2624bdb3dd
Source dataset
uspto-grants-1998_12
Patent number
US05849753

Reaction notes

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