2-Chloroethylamine → HCID 19606232, compound

HRID 1603743Notes

Reaction equation

HRID 1603743 reaction equation
Cl[CH2:2][CH2:3][NH2:4].[CH2:5]([C:7]1[CH:12]=[CH:11][C:10]([N:13]=[C:14]=[O:15])=[CH:9][CH:8]=1)[CH3:6].[H-].[Na+]>C(OCC)C.O1CCCC1>[CH2:5]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:2][CH2:3][NH:4][C:14]2=[O:15])=[CH:9][CH:8]=1)[CH3:6]

Participants

6

Reactant 3

HCID 133692-ChloroethylamineHCID 24758Sodium hydrideHCID 900074-Ethylphenyl isocyanate

Product 1

HCID 19606232HCID 19606232, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3.98 g of 2-chloroethylamine in 30 ml of diethyl ether, a solution of 3.68 g of 4-ethylphenyl isocyanate in 15 ml of tetrahydrofuran was added dropwise under ice cooling. After the resultant mixture was stirred at room temperature for 30 minutes, diethyl ether was added, followed by the collection of precipitated crystals by filtration. The crystals so obtained were added under ice cooling to a suspension of 10.8 g of 60%-sodium hydride in 35 ml of tetrahydrofuran, followed by stirring at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure, to which 1N hydrochloric acid was added. Resulting crystals were collected by filtration and washed with n-hexane, whereby 3.64 g of the title compound were obtained (yield: 89%).

Workup

  1. filtrationfollowed by the collection of precipitated crystals by filtration
  2. customThe crystals so obtained
  3. concentrationThe reaction mixture was concentrated under reduced pressure, to which 1N hydrochloric acid
  4. additionwas added
  5. customResulting crystals
  6. filtrationwere collected by filtration
  7. washwashed with n-hexane

Sources & evidence

ORD record
ord-847e8389326943caad879974427351e8
Source dataset
uspto-grants-1999_11
Patent number
US05990139

Reaction notes

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