Ammonia → (3-Benzylphenyl)thiourea

HRID 2237609

Reaktionsgleichung

Reaktionsgleichung von HRID 2237609
[CH2:1]([C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15](N1C=CN=C1)([N:17]1C=CN=C1)=[S:16].N>ClCCl.CO.C(OC(=O)C)C>[CH2:1]([C:8]1[CH:9]=[C:10]([NH:11][C:15]([NH2:17])=[S:16])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 3

HCID 222AmmoniaHCID 802641,1'-ThiocarbonyldiimidazoleHCID 3088693-Benzylaniline

Produkt 1

HCID 5277306(3-Benzylphenyl)thiourea

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 3-benzylaniline (183 mg, 1 mmol) and 1,1′-thiocarbonyldiimidazole (197 mg, 1.1 mmol) in dichloromethane (5 ml) is stirred at room temperature for 1.5 hours. 2 M ammonia in methanol (2.5 ml) is added to the solution and the mixture is stirred at room temperature overnight. The solution is diluted with ethylacetate, and the organic layer is washed with 5% HCl, saturated NaHCO3, and brine, and dried (anhydrous Na2SO4). The crude product is recrystallized from ethylacetate and petroleum ether to give the desired product as a white powder. 1H NMR (300 Hz, CDCl3) δ 7.93 (br s, 1H, NH), 7.73-7.02 (m, 9H, Aryl H), 6.06 (br s, 2H, NH2), 3.98 (s, 2H, CH2). MS (APCI) m/z 243 [M+H]±.

Aufarbeitung

  1. washthe organic layer is washed with 5% HCl, saturated NaHCO3, and brine
  2. dry with materialdried (anhydrous Na2SO4)
  3. customThe crude product is recrystallized from ethylacetate and petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-d3a02f982036425fb54709afc3e41d80
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07718671B2

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