Water → HCID 18630729, compound

HRID 1059524Notes

Reaction equation

HRID 1059524 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].C(N(CC)CC)C.Cl.[C:20]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1)#[N:21].O>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH:27][CH2:26][C:25]2[CH:28]=[CH:29][C:22]([C:20]#[N:21])=[CH:23][CH:24]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27333153-IsocyanatobenzonitrileHCID 99422504-(Aminomethyl)benzonitrile hydrochloride

Product 1

HCID 18630729HCID 18630729, compoundYield 14.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

m-Cyanophenyl isocyanate (2.0 g, 13.9 mmol) and triethylamine (3.09 g, 30.5 mmol) in dimethylformamide (30 ml) was cooled to 0° C. and p-cyanobenzylamine hydrogen chloride (2.3 g, 13.9 mmol) in dimethylformamide (10 ml) was added dropwise. The reaction was thawed to ambient temperature and was stirred for 18 h. The reaction was poured into water and extracted with ethyl acetate. The ethyl acetate extract was washed with 1N HCl and brine, then dried (Na2SO4) and evaporated. The crude product was purified by flash chromatography on silica gel with 1:1 hexane:ethyl acetate as an eluent; there was obtained 0.54 g of pure N-(3-cyanophenyl)-N′-((4-cyanophenyl)methyl)urea; LRMS (M+H)+ m/z 294.

Workup

  1. customwas thawed to ambient temperature
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with 1N HCl and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe crude product was purified by flash chromatography on silica gel with 1:1 hexane

Sources & evidence

ORD record
ord-d3c57620a31e45a79da97128ae37e1f1
Source dataset
uspto-grants-2003_02
Patent number
US06521614B1

Reaction notes

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