Triethylamine → HCID 12889667, compound

HRID 894328Notes

Reaction equation

HRID 894328 reaction equation
[CH:1](=[N:8][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([NH:13][C:14](=[O:17])[O:15][CH3:16])[CH:11]=[CH2:12].C(N(CC)CC)C>C(OCC)C>[CH3:16][O:15][C:14]([NH:13][CH2:10][CH:11]1[O:9][N:8]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:12]1)=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12143(Z)-Benzaldehyde oximeHCID 186042Methyl hydrogen prop-2-en-1-ylcarbonimidate

Product 1

HCID 12889667HCID 12889667, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
15 °C

Procedure

A 24 g. portion of benzaldoxime was chlorinated, isolated and dissolved in diethyl ether. The solution was cooled to 15° C., and 46 g. of methyl allylcarbamate was added. Sixty ml. of triethylamine was then added dropwise, keeping the temperature below 20° C. The mixture was stirred for 3 hours, and filtered. The filtrate was evaporated to dryness, and the residue was washed with water and filtered again. The solids were identified as 32 g. of product, m.p. 102°-103° C., NMR singlets at 3.63 and 5.48 ppm., multiplets at 2.82-3.80, 4.57-5.08, 7.13-7.50 and 7.45-7.77 ppm.

Workup

  1. customisolated
  2. customthe temperature below 20° C
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. washthe residue was washed with water
  6. filtrationfiltered again

Sources & evidence

ORD record
ord-f3849fc1a3da4249ba44783383b682ee
Source dataset
uspto-grants-1981_08
Patent number
US04283403

Reaction notes

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