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

HRID 1901394ノート

反応式

HRID 1901394 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-765656fb180749249d5ded94745e1ac8
出典データセット
uspto-grants-1996_11
特許番号
US05578242

反応ノート

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