N,N'-Dimethylethylenediamine → 1-Butyl-3-(3-methoxyphenyl)urea

HRID 2179263

Reaction equation

HRID 2179263 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:9]([NH:13][C:14]([NH2:16])=[O:15])[CH2:10][CH2:11][CH3:12].I[C:18]1[CH:19]=[C:20]([O:24][CH3:25])[CH:21]=[CH:22][CH:23]=1.CNCCNC>[Cu]I.C1(C)C=CC=CC=1>[CH2:9]([NH:13][C:14]([NH:16][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)=[O:15])[CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11595ButylureaHCID 62657Potassium Phosphate, TribasicHCID 69839Benzene, 1-iodo-3-methoxy-

Product 1

HCID 40535891-Butyl-3-(3-methoxyphenyl)ureaYield 85%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A test tube was charged with CuI (10 mg, 0.05 mmol, 0.05 equiv), K3PO4 (425 mg, 2.0 mmol, 2.0 equiv), butylurea (232 mg, 2.0 mmol, 2.0 equiv), filled with argon. 3-Iodoanisole (119 μL, 1.0 mmol, 1.0 equiv), N,N′-dimethylethylendiamine (11 μL, 0.10 mmol, 0.10 equiv) and dry toluene (1.0 mL) were added under argon. The test tube was sealed and the reaction mixture was stirred at 110° C. for 24 h. The resulting suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel, eluting with diethyl ether. The filtrate was concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (2×20 cm; pentane:diethyl ether 1:2) provided 188 mg (85% yield) of the title compound as a light yellow oil.

Workup

  1. additionfilled with argon
  2. customThe test tube was sealed
  3. temperatureThe resulting suspension was cooled to room temperature
  4. filtrationfiltered through a 0.5×1 cm pad of silica gel
  5. washeluting with diethyl ether
  6. concentrationThe filtrate was concentrated in vacuo
  7. customPurification of the residue by flash chromatography on silica gel (2×20 cm; pentane:diethyl ether 1:2)

Sources & evidence

ORD record
ord-81ad4315ae7b4f9b9dd49bb1db79838b
Source dataset
uspto-grants-2015_06
Patent number
US09067955B2

Linked notes

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