Butylamine → 1-Butyl-3-(3-cyanophenyl)thiourea

HRID 1241947Notes

Reaction equation

HRID 1241947 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].C(=O)(O)[O-].[Na+].[C:15](Cl)(Cl)=[S:16].[CH2:19]([NH2:23])[CH2:20][CH2:21][CH3:22]>C(Cl)(Cl)Cl>[CH2:19]([NH:23][C:15]([NH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[CH:3]=1)=[S:16])[CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 8007ButylamineHCID 10040ThiophosgeneHCID 167023-AminobenzonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 23461541-Butyl-3-(3-cyanophenyl)thioureaYield 87.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a 250 mL flask was added 3-aminobenzonitrile (0.59 g, 5.0 mmol), CHCl3 (25 mL) and saturated sodium bicarbonate (25 mL). To the well-stirred mixture was added dropwise thiophosgene (0.39 mL, 5.1 mmol). After 2 h butylamine (0.50 mL, 5.1 mmol) was added dropwise and stirred 1 h. The reaction mixture was then extracted with CHCl3, concentrated under reduced pressure, and chromatographed (silica gel, 2:98 MeOH/DCM) to yield 1-butyl-3-(3-cyanophenyl)thiourea (1.02 g, 87%) as a white solid: TLC (2:98 MeOH/DCM Rf 0.47).

Workup

  1. extractionThe reaction mixture was then extracted with CHCl3
  2. concentrationconcentrated under reduced pressure
  3. customchromatographed (silica gel, 2:98 MeOH/DCM)

Sources & evidence

ORD record
ord-d045eb7d6e9b4c2e930c9c4617553ce1
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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