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Diisopropylamine → 1-Ethyl-3-(3,4,5-trimethoxyphenylthio)-1-(2-thienyl)propyl isocyanide

HRID 1722743
Notes
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Reaction equation

HRID 1722743 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.CCCCCC.C([N-]C(C)C)(C)C.[Li+].[S:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[CH:32]([N+:35]#[C-:36])[CH2:33][CH3:34].[CH3:37][O:38][C:39]1[CH:40]=[C:41]([S:49][CH2:50][CH2:51]Cl)[CH:42]=[C:43]([O:47][CH3:48])[C:44]=1[O:45][CH3:46]>O1CCCC1.CCOCC.C(O)(=O)C>[CH2:33]([C:32]([N+:35]#[C-:36])([C:28]1[S:27][CH:31]=[CH:30][CH:29]=1)[CH2:51][CH2:50][S:49][C:41]1[CH:40]=[C:39]([O:38][CH3:37])[C:44]([O:45][CH3:46])=[C:43]([O:47][CH3:48])[CH:42]=1)[CH3:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 149941832-(3,4,5-Trimethoxyphenylthio)ethyl chlorideHCID 152885881-(2-Thienyl)propyl isocyanideHCID 178418244HCID 178418244, compound

Product 1

HCID 10691010
1-Ethyl-3-(3,4,5-trimethoxyphenylthio)-1-(2-thienyl)propyl isocyanide
Yield 74.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of diisopropylamine (2.65 g) in tetrahydrofuran is cooled to -60° C. and 1.6M n-butyl lithium/hexane solution (14 ml) is added dropwise thereto in nitrogen atmosphere. The mixture is stirred at the same temperature, whereby the solution containing lithium diisopropylamide is obtained. A solution of 1-(2-thienyl)propyl isocyanide (2.8 g) in tetrahydrofuran is added dropwise to the solution obtained above at -60° C. and the mixture is stirred at the same temperature for 20 minutes. A solution of 2-(3,4,5-trimethoxyphenylthio)ethyl chloride (5.9 g) in tetrahydrofuran is added dropwise to the mixture at -60° C. and the mixture is stirred at -30° C. in nitrogen atmosphere for 2 hours. Acetic acid is added to the mixture to cease the reaction and ether is added to the reaction mixture. The mixture is washed, dried and concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography, whereby 1-ethyl-3-(3,4,5-trimethoxyphenylthio)-1-(2-thienyl)propyl isocyanide (5.2 g) is obtained as red oil.

Workup

  1. customis obtained
  2. customobtained above at -60° C.
  3. stirringthe mixture is stirred at the same temperature for 20 minutes
  4. stirringthe mixture is stirred at -30° C. in nitrogen atmosphere for 2 hours
  5. additionis added to the reaction mixture
  6. washThe mixture is washed
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customto remove solvent
  10. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-4bc0e71f055b4fac883f1a2cebd824c3
Source dataset
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04857543

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes