Ammonia → (3-Benzylphenyl)thiourea

HRID 2237609

Reaction equation

HRID 2237609 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

HCID 5277306(3-Benzylphenyl)thiourea

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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]±.

Workup

  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

Sources & evidence

ORD record
ord-d3a02f982036425fb54709afc3e41d80
Source dataset
uspto-grants-2010_05
Patent number
US07718671B2

Linked notes

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