Isobutylamine → HCID 13254213, compound

HRID 905261Notes

Reaction equation

HRID 905261 reaction equation
[CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].[Cl:6][CH2:7][CH2:8][N:9]=[C:10]=[O:11]>C(OCC)C>[CH2:1]([NH:5][C:10]([NH:9][CH2:8][CH2:7][Cl:6])=[O:11])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 160352-Chloroethyl isocyanate

Product 1

HCID 13254213HCID 13254213, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-5 °C

Procedure

Isobutylamine (7.3 g, 0.1 mol) was dissolved in 20 ml of diethyl ether and cooled to less than 5° C. Chloroethyl isocyanate (10.5 g, 0.1 mol) dissolved in 15 ml of ether was added maintaining a temperature between 0° and 5° C. with vigorous stirring. Stirring continued an additional 2 hrs. the mixture was cooled to -5° C., and the product (4.1 g, 46%) was filtered and dried in vacuo for 18 hrs. over KOH, MP 79.5° C. (decomposes). IR analysis showed peaks at 1630/cm (C=O) and 1585/cm (N--C=O). NMR: Doublet at 0.9 ppm (J=6.4 Hz), multiplet (1H) at 2.1 ppm, quartet (2H) at 2.9 ppm (J=6.4 Hz), multiplet (4H) at 3.5 ppm.

Workup

  1. temperaturecooled to less than 5° C
  2. additionwas added
  3. temperaturemaintaining a temperature between 0° and 5° C. with vigorous stirring
  4. filtrationthe product (4.1 g, 46%) was filtered
  5. customdried in vacuo for 18 hrs

Sources & evidence

ORD record
ord-00845aac159444a7a376562adf592176
Source dataset
uspto-grants-1983_12
Patent number
US04423076

Reaction notes

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