1,3-Propanedithiol → N,N'-Dicyclohexylurea

HRID 511735Notes

Reaction equation

HRID 511735 reaction equation
S1C=CC(CC(O)=[O:8])=C1.C(S)CCS.[CH:15]1([N:21]=[C:22]=[N:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>CN(C)C1C=CN=CC=1.C(Cl)Cl.CC(C)=O>[CH:24]1([NH:23][C:22]([NH:21][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)=[O:8])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

7

Reactant 3

HCID 80131,3-PropanedithiolHCID 10868DicyclohexylcarbodiimideHCID 234043-Thiophenacetic acid

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 180AcetoneSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

As shown in Reaction 1, 2-(thiophene-3-yl)acetic acid) (1 g, 7.03 mmol), propane-1,3-dithiol (0.753 g, 7.03 mmol), and 4-dimethylaminopyridine (4-DMAP) (2.014 g, 1.75 mol) were dissolved in 80 ml of methylene chloride in a three-neck round bottom flask, after which stirring was performed at 60° C. in a nitrogen atmosphere. The stirred mixture solution was slowly added with N,N′-dicyclohexylcarbodiimide (DCC) (2.89 g, 14.06 mol) dissolved in 20 ml of methylene chloride, and was then allowed to react for 9 hours. The reaction solution was washed using saturated aqueous Na2CO3, dried over MgSO4, and filtered. The remaining solvent was removed by rotary evaporation to obtain a yellowish solution. This solution was diluted with acetone, and cooled to 0° C., to obtain residual 1,3-dicyclohexylurea (“DCU”) as a precipitate. This precipitate was removed by filtration through a paper filter, and addition of acetone and removal of the DCU precipitate were repeated until DCU precipitate was no longer evident in the solution. Finally, the remaining solvent was removed by rotary evaporation, and the crude purified using a silica column eluted with a solution of methylene chloride and methanol (60:1 v/v), thereby producing after collection of the fractions and removal of the solvent, S-3-mercaptopropyl-2-(thiophene-3-yl)ethanethioate (“MTE”) (the monomer) as a pure yellow compound. The characteristic H1-NMR spectrum (in acetone-d6) of the product is shown in FIG. 1.

Workup

  1. customwas performed at 60° C. in a nitrogen atmosphere
  2. customto react for 9 hours
  3. washThe reaction solution was washed
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe remaining solvent was removed by rotary evaporation
  7. customto obtain a yellowish solution

Sources & evidence

ORD record
ord-bd5a8650bdec4eb995b207758e9e853a
Source dataset
uspto-grants-2015_08
Patent number
US09099221B2

Reaction notes

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