Isoamylamine → HCID 13254212, compound

HRID 905260Notes

Reaction equation

HRID 905260 reaction equation
[CH2:1]([NH2:6])[CH2:2][CH:3]([CH3:5])[CH3:4].[Cl:7][CH2:8][CH2:9][N:10]=[C:11]=[O:12]>CCOCC>[CH2:1]([NH:6][C:11]([NH:10][CH2:9][CH2:8][Cl:7])=[O:12])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 7894IsoamylamineHCID 160352-Chloroethyl isocyanate

Product 1

HCID 13254212HCID 13254212, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Isopentylamine (8.7 g, 0.1 mol) was dissolved in 100 ml of anhydrous ether and cooled to less than 10° C. 2-Chloroethyl isocyanate (10.5 g, 0.1 mol) was dissolved in 20 ml of ether and added to the rapidly stirring reaction mixture at less than 10° C. Stirring continued 1 hr. longer and the preciptiate was filtered and washed with four 20 ml portions of chilled ether. After drying in vacuo overnight, 16.5 g (85%) of product obtained as a white powder, MP 58°-9° C. IR analysis showed peaks at 1620/cm (C=O) and 1575/cm (N--C=O). NMR showed a doublet (6H, J=7 Hz) at 0.9 ppm, a triplet (2H, J=7 Hz) at 1.4 ppm, a multiplet (1H) at 1.8 ppm, a multiplet (1H) at 3.2 ppm, a multiplet (4H) at 3.6 ppm, a singlet ( 1H) at 5.7 ppm, and a singlet (1H) at 6.0 ppm.

Workup

  1. temperaturecooled to less than 10° C
  2. additionadded to the
  3. customreaction mixture at less than 10° C
  4. stirringStirring
  5. filtrationlonger and the preciptiate was filtered
  6. washwashed with four 20 ml portions of chilled ether
  7. dry with materialAfter drying in vacuo overnight, 16.5 g (85%) of product
  8. customobtained as a white powder, MP 58°-9° C

Sources & evidence

ORD record
ord-87866d66f990414a85bdfd2ed8aa338f
Source dataset
uspto-grants-1983_12
Patent number
US04423076

Reaction notes

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