Ammonia → Thiourea, [4-(pentyloxy)phenyl]-

HRID 2237610Notes

Reaction equation

HRID 2237610 reaction equation
[CH2:1]([O:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[C:14](N1C=CN=C1)([N:16]1C=CN=C1)=[S:15].N>ClCCl.CO>[CH2:1]([O:6][C:7]1[CH:8]=[CH:9][C:10]([NH:11][C:14]([NH2:16])=[S:15])=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 802641,1'-ThiocarbonyldiimidazoleHCID 94500Benzenamine, 4-(pentyloxy)-

Product 1

HCID 5277352Thiourea, [4-(pentyloxy)phenyl]-

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

4-Pentyloxyaniline (370 ml, 2 mmol) in dichloromethane (3 ml) is added to a solution of 1,1′-thiocarbonyldiimidazole (537 mg, 3 mmol) in dichloromethane (5 ml) at room temperature and the mixture is stirred at room temperature for 30 minutes. 2 N Ammonia in methanol (30 ml) is added to the solution, and the solution is stirred for additional 1 hour at room temperature. The solvent is removed, and the product extracted with ethylacetate and H2O. The crude product is recrystallized from dichloromethane and hexane to afford the thiourea as a white solid. 1H NMR (300 Hz, CDCl3) δ 7.92 (s, 1H, NH), 7.15 (d, J=8.4 Hz, 2H, Aryl H), 6.92 (d, J=8.4 Hz, 2H, Aryl H), 6.0 (br s, 2H, NH2), 3.95 (t, J=6.6 Hz, 2H, CH2), 1.79 (m, 2H, CH2), 1.44-1.38 (m, 4H, (CH2)2), 0.94 (t, J=7.2 Hz, 3H, CH3). MS (APCI) m/z 239 [M+H]±.

Workup

  1. stirringthe solution is stirred for additional 1 hour at room temperature
  2. customThe solvent is removed
  3. extractionthe product extracted with ethylacetate and H2O
  4. customThe crude product is recrystallized from dichloromethane and hexane

Sources & evidence

ORD record
ord-576896d9a9f741978b4487d4635f0763
Source dataset
uspto-grants-2010_05
Patent number
US07718671B2

Reaction notes

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