Water → HCID 21893438, compound

HRID 1358683Notes

Reaction equation

HRID 1358683 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[S:7][C:8]([CH:11]([CH3:14])[CH2:12][NH2:13])=[CH:9][CH:10]=2)=[CH:2]1.[S:15](C[N+]#[C-])([C:18]1[CH:24]=CC(C)=C[CH:19]=1)(=[O:17])=[O:16].CC(C)([O-])C.[K+].O>COCCOC.C(O)(C)(C)C>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[S:7][C:8]([CH:11]([CH3:14])[CH2:12][NH:13][S:15]([CH:18]([CH3:24])[CH3:19])(=[O:17])=[O:16])=[CH:9][CH:10]=2)=[CH:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 161915Tosylmethyl isocyanideHCID 21893418HCID 21893418, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21893438HCID 21893438, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
-5 °C

Procedure

2-[2-(thien-3-yl)-5-thienyl]propylamine To a −15° C. solution of 1.1 g (5.3 mmol) of the material prepared in step A and 1.05 g (5.35 mmol) of tosylmethyl isocyanide in 18 ml of DME, a hot solution of 1.07 g (9.54 mmol) of potassium tert-butoxide in 5 ml of tert-butanol was added slowly. The mixture was stirred at −5° C. for 45 min and 2 h at ambient temperature. Water was added and extracted three times with diethyl ether. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The crude material was dissolved in 15 ml of diethyl ether and then was added to a suspension of 218 mg (5.75) of lithium aluminum hydride in 5 ml of diethyl ether. The mixture was stirred at ambient temperature for 2 h. Na2SO410H2O was added, and the mixture stirred for 30 min at ambient temperature. The solid was filtered and the organic solution was concentrated in vacuo. Chromatography (150 g of silica gel, ethyl acetate/hexane/methanol 10/10/1) of the residue afforded 250 mg (22%) of the title compound.

Workup

  1. extractionextracted three times with diethyl ether
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude material was dissolved in 15 ml of diethyl ether
  6. additionwas added to a suspension of 218 mg (5.75) of lithium aluminum hydride in 5 ml of diethyl ether
  7. stirringThe mixture was stirred at ambient temperature for 2 h
  8. additionNa2SO410H2O was added
  9. stirringthe mixture stirred for 30 min at ambient temperature
  10. filtrationThe solid was filtered
  11. concentrationthe organic solution was concentrated in vacuo

Sources & evidence

ORD record
ord-10583c413eba49899651f57edaa16e2d
Source dataset
uspto-grants-2003_07
Patent number
US06596716B2

Reaction notes

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