2-Chloroethyl isocyanate → HCID 13254210, compound

HRID 905258Notes

Reaction equation

HRID 905258 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][NH2:5].[Cl:8][CH2:9][CH2:10][N:11]=[C:12]=[O:13]>C(OCC)C>[CH2:4]([NH:5][C:12]([NH:11][CH2:10][CH2:9][Cl:8])=[O:13])[CH2:3][C:2]([CH3:7])([CH3:6])[CH3:1]

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 197093,3-Dimethylbutylamine

Product 1

HCID 13254210HCID 13254210, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 5 g quantity of 3,3-dimethyl butylamine (0.5 mol) was dissolved in 30 ml of anhydrous diethyl ether and stirred on an ice bath. 2-Chloroethyl isocyanate (5.25 g, 0.5 mol) dissolved in 15 ml of ether was added maintaining a temperature of 10° C. or less, and stirring continued for 2 hrs. Filtering the product and washing with four 5 ml portions of chilled ether afforded 6.2 g (60%) which melted at 84° C. (decomposes). IR analysis showed peaks at 1625/cm (C=O) and 1580/cm (N--C=O). NMR: singlet (9H) at 0.9 ppm, multiplet (2H) at 1.3 ppm, multiplet (2H) at 3.2 ppm, multiplet (4H) at 3.5 ppm, singlet (1H) at 5.5 ppm, and singlet (1H) at 5.7 ppm.

Workup

  1. additionwas added
  2. temperaturemaintaining a temperature of 10° C. or less
  3. stirringstirring
  4. filtrationFiltering the product
  5. washwashing with four 5 ml portions of chilled ether
  6. customafforded 6.2 g (60%) which melted at 84° C. (decomposes)

Sources & evidence

ORD record
ord-27295761e7904dc7a82c9ef2cf9f9758
Source dataset
uspto-grants-1983_12
Patent number
US04423076

Reaction notes

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