Hydrochloric Acid → HCID 22137208, compound

HRID 1827301Notes

Reaction equation

HRID 1827301 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([S:26](N(C)C)(=O)=O)=[C:22]([SH:32])[CH:21]=3)=[CH:16][CH:15]=2)[CH:5]=[CH:6][C:7]=1[S:8](N(C)C)(=O)=O.C1COCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C(Cl)Cl.CCOC(C)=O>[SH:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][C:23]([SH:26])=[C:22]([SH:32])[CH:21]=3)=[CH:18][CH:19]=2)[CH:5]=[CH:6][C:7]=1[SH:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 22137210HCID 22137210, compound

Product 1

HCID 22137208HCID 22137208, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,3″-dimercapto-4,4″-bis(N,N′-dimethylaminosulfonyl)-1,1′:4′,1″-terphenyl (508 mg, 1 mmol) synthesized in process 3-a is dissolved into 30 ml of absolute THF, lithium aluminium hydride (445 mg, 12 mmol, 12 eq) is added at the temperature of 0° C., then the reacting solution is refluxed for 24 hours. The obtained reaction mixture is poured into ice water, and adjusted the pH to 1 or less by adding hydrochloric acid, that is, acidified. Deposited green precipitate is removed by suction filtration, then the filtrate is washed by methylene chloride completely. After that, the filtrate is extracted by acid-base extraction (CH2Cl2), the separated organic phase is dried up using magnesium sulfate and recrystallized. Solvent is evaporated off under vacuum condition and the obtained crude product is isolated by a column chromatography (φ=20 mm, h=10 mm; AcOEt), further refined by recrystallization (CH2Cl2) and 3,3″,4,4″-tetramercapto-1,1′:4′,1″-terphenyl (78 mg, 22%) is obtained as a light yellowish crystal (compound J).

Workup

  1. additionis added at the temperature of 0° C.
  2. temperaturethe reacting solution is refluxed for 24 hours
  3. customThe obtained reaction mixture
  4. customDeposited green precipitate is removed by suction filtration
  5. washthe filtrate is washed by methylene chloride completely
  6. extractionAfter that, the filtrate is extracted by acid-base extraction (CH2Cl2)
  7. customthe separated organic phase is dried up
  8. customrecrystallized
  9. customSolvent is evaporated off under vacuum condition
  10. customthe obtained crude product

Sources & evidence

ORD record
ord-df506b8067f245d490b215eeadff446b
Source dataset
uspto-grants-2006_05
Patent number
US07053173B2

Reaction notes

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