2-Chloroethyl isocyanate → HCID 15615086, compound

HRID 1988358Notes

Reaction equation

HRID 1988358 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]=[C:5]=[O:6].[C:7]([C:11]1[CH:16]=[C:15]([NH2:17])[CH:14]=[C:13]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:12]=1[OH:22])([CH3:10])([CH3:9])[CH3:8]>CN(C=O)C.C(OCC)(=O)C.O>[CH3:21][C:18]([C:13]1[CH:14]=[C:15]([NH:17][C:5]([NH:4][CH2:3][CH2:2][Cl:1])=[O:6])[CH:16]=[C:11]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:12]=1[OH:22])([CH3:19])[CH3:20]

Participants

6

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 3142204-Amino-2,6-di-tert-butylphenol

Product 1

HCID 15615086HCID 15615086, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

0.17 ml (2 mmol) of chloroethylisocyanate is added to a flask containing a solution of 0.5 g (2 mmol) of intermediate 10.2 in 5 ml of DMF. The reaction mixture is agitated for 2 hours at 23° C. and finally diluted with 100 ml of ethyl acetate and 25 ml of water. After decantation, the organic solution is washed with 25 ml of water, twice with 25 ml of salt water and finally dried over magnesium sulphate. After filtration and evaporation, the residue is taken up in isopentane in order to finally produce the expected product, in the form of a pink solid, with a yield of 83%. Melting point: 169-171° C.

Workup

  1. washAfter decantation, the organic solution is washed with 25 ml of water, twice with 25 ml of salt water
  2. dry with materialfinally dried over magnesium sulphate
  3. filtrationAfter filtration and evaporation

Sources & evidence

ORD record
ord-d9fc263484ce471da4f2076f04d73cf2
Source dataset
uspto-grants-2009_06
Patent number
US07553976B2

Reaction notes

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