Dicyclohexylcarbodiimide → S-(4-Cyanophenyl) 4-butylsulphanylthiobenzoate

HRID 1901398Notes

Reaction equation

HRID 1901398 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([S:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=O)=[CH:23][CH:22]=1)[CH2:17][CH2:18][CH3:19].[C:30]([C:32]1[CH:37]=[CH:36][C:35]([SH:38])=[CH:34][CH:33]=1)#[N:31]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:16]([S:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([S:38][C:35]2[CH:36]=[CH:37][C:32]([C:30]#[N:31])=[CH:33][CH:34]=2)=[O:27])=[CH:28][CH:29]=1)[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 4217574-(Butylthio)benzoic acidHCID 5850584-Thiobenzonitrile

Product 1

HCID 86750023S-(4-Cyanophenyl) 4-butylsulphanylthiobenzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

N,N'-dicyclohexylcarbodiimide (0.99 g, 0.005 mol), was added in one portion to a stirred solution of compound 2 (1.04 g, 0.005 mol), compound 10 (0.56 g, 0.004 mol) and 4-(dimethylamino)pyridine (0.20 g, 0.002 mol), in dry dichloromethane (50 ml) at room temperature. The reaction mixture was stirred at room temperature overnight. The product was extracted into ether (200 ml) and was washed with aqueous potassium hydroxide solution (5%, 2×250 ml). The ether layer was evaporated in vacuo and the product was purified by column chromatography [silica gel/petroleum fraction (bp 40°-60° C.), dichloromethane, 1:1] and was recrystallised from ethanol to afford a white solid which was dried in vacuo (P2O5).

Workup

  1. extractionThe product was extracted into ether (200 ml)
  2. washwas washed with aqueous potassium hydroxide solution (5%, 2×250 ml)
  3. customThe ether layer was evaporated in vacuo
  4. customthe product was purified by column chromatography [silica gel/petroleum fraction (bp 40°-60° C.), dichloromethane, 1:1]
  5. customwas recrystallised from ethanol
  6. customto afford a white solid which
  7. dry with materialwas dried in vacuo (P2O5)

Sources & evidence

ORD record
ord-58874b39396e48ada5ed45e61abda626
Source dataset
uspto-grants-1996_11
Patent number
US05578242

Reaction notes

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