Water → HCID 12237082, compound

HRID 1940878Notes

Reaction equation

HRID 1940878 reaction equation
[C:1]1([N:7]=[C:8]=S)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.[OH2:19]>C(Cl)Cl>[C:1]1([NH:7][C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7673Phenyl IsothiocyanateHCID 759192-Pyridineethanamine

Product 1

HCID 12237082HCID 12237082, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Phenyl isothiocyanate (1.35 g, 10 m mol) was dissolved in 7 ml of anhydrous methylene chloride, and the solution was cooled in an ice bath. Thereto was added 1.2 g (10 m mol) of 2-(2-aminoethyl)pyridine dissolved in 3 ml of anhydrous methylene chloride. The mixture was stirred at room temperature for 15 minutes. The reaction mixture was mixed with water, followed by extraction with methylene chloride. The extract was dried with anhydrous potassium carbonate and concentrated to obtain 2.8 g of a crude product. It was purified by silica gel column chromatography (chloroform:methanol=9/1) to obtain 2.3 g (yield: 88%) of N-phenyl-N'-2-pyridylethylurea.

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. extractionfollowed by extraction with methylene chloride
  3. dry with materialThe extract was dried with anhydrous potassium carbonate
  4. concentrationconcentrated
  5. customto obtain 2.8 g of a crude product
  6. customIt was purified by silica gel column chromatography (chloroform:methanol=9/1)

Sources & evidence

ORD record
ord-eb0f3a6448a3410d80156c79eccd73ba
Source dataset
uspto-grants-1997_12
Patent number
US05700935

Reaction notes

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