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

HRID 1901394Notes

Reaction equation

HRID 1901394 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].[N:30]([C:33]1[CH:38]=[CH:37][C:36]([SH:39])=[CH:35][CH:34]=1)=[C:31]=[S:32]>ClCCl>[CH2:16]([S:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([S:39][C:36]2[CH:37]=[CH:38][C:33]([N:30]=[C:31]=[S:32])=[CH:34][CH:35]=2)=[O:27])=[CH:28][CH:29]=1)[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 4217574-(Butylthio)benzoic acidHCID 233673904-Isothiocyanatobenzene-1-thiol

Product 1

HCID 86750022S-(4-Isothiocyanatophenyl) 4-butylsulphanylthiobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N'-dicyclohexylcarbodiimide (1.95 g, 0.009 mol), was added in one portion to a stirred solution of compound 2 (1.67 g, 0.008 mol), compound 3 (1.59 g, 0.009 mol) and 4-(N-pyrrolidino)pyridine (0.39 g, 0.003 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 cyclohexane to afford a white solid which was dried in vacuo.

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 cyclohexane
  6. customto afford a white solid which
  7. customwas dried in vacuo

Sources & evidence

ORD record
ord-765656fb180749249d5ded94745e1ac8
Source dataset
uspto-grants-1996_11
Patent number
US05578242

Reaction notes

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