Phenethyl Isothiocyanate → 1-(4-Chloro-2-(alpha-hydroxybenzyl)benzyl)-3-phenethylthiourea

HRID 442496

Reaktionsgleichung

Reaktionsgleichung von HRID 442496
[NH2:1][CH2:2][C:3]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:4]=1[CH:5]([OH:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:18]([N:26]=[C:27]=[S:28])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO.C(N(CC)CC)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:3]([CH2:2][NH:1][C:27]([NH:26][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[S:28])=[C:4]([CH:5]([OH:12])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:13]=1

Komponenten

5

Edukt 2

HCID 16741Phenethyl IsothiocyanateHCID 12241006Benzenemethanol,2-(aminomethyl)-5-chloro-a-phenyl-

Produkt 1

HCID 214154601-(4-Chloro-2-(alpha-hydroxybenzyl)benzyl)-3-phenethylthiourea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

2-aminomethyl-5-chlorobenzhydrol (10 g; 0.04 mole) in 100 ml methanol and 2 ml triethylamine was treated dropwise with a solution of phenethyl isothiocyanate (8.6 g; 0.053 mole) in 25 ml of methanol. After 16 hours at room temperature the reaction mixture was evaporated and the residue was extracted with petroleum ether. The residual oil was recrystallized from diisopropyl ether to yield 1-(4-chloro-2-(α-hydroxybenzyl)benzyl)-3-phenethylthiourea as a white powder (M.Pt. 97° -- 101° ).

Aufarbeitung

  1. customAfter 16 hours at room temperature the reaction mixture was evaporated
  2. extractionthe residue was extracted with petroleum ether
  3. customThe residual oil was recrystallized from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-93903d4497c1482bb535b4bb2fd9bcc5
Quelldatensatz
uspto-grants-1977_08
Patentnummer
US04045572

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