Formaldehyde → 4-Diethylaminobenzaldehyde N-2,3-epoxvpropyl-N-phenylhydrazone

HRID 1791092Notes

Reaction equation

HRID 1791092 reaction equation
[O:1]1[CH2:28][CH:2]1[CH2:3][N:4]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[N:5]=[CH:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH2:20][CH3:21])[C:12]3C([C:18]=2[CH:19]=1)=CC=C[CH:13]=3.C1(NN=CC2C=CC3N(CC)C4C(C=3C=2)=CC=CC=4)C=CC=CC=1.C1(NN=CC2C=CC(N(CC)CC)=CC=2)C=CC=CC=1.C=O>>[O:1]1[CH2:28][CH:2]1[CH2:3][N:4]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[N:5]=[CH:6][C:7]1[CH:19]=[CH:18][C:10]([N:11]([CH2:12][CH3:13])[CH2:20][CH3:21])=[CH:9][CH:8]=1

Participants

5

Reactant 4

HCID 712Formaldehyde2×HCID 6224694-Diethylaminobenzaldehyde phenylhydrazoneHCID 688623579-Ethyl-3-carbazolecarbaldehyde phenylhydrazoneHCID 731765569-Ethyl-3-carbazolecarbaldehyde n-2,3-epoxypropyl-n-phenylhydrazone

Product 1

HCID 40800804-Diethylaminobenzaldehyde N-2,3-epoxvpropyl-N-phenylhydrazone

Procedure

4-(Diethylamino)benzaldehyde N-2,3-epoxypropyl-N-phenylhydrazone was prepared according to the preparation procedure above for 9-ethyl-3-carbazolecarboxaldehyde N-2,3-epoxypropyl-N-phenylhydrazone except that 9-ethyl-3-carbazolecarboxaldehyde phenylhydrazone was replaced by 4-(diethylamino)benzaldehyde phenylhydrazone and the product was recrystallized from diethyl ether. The yield of 4-(diethylamino)benzaldehyde N-2,3-epoxypropyl-N-phenylhydrazone was 69%. The product had a melting point of 79–80.5° C. when recrystallized from diethyl ether. A 1H-NMR spectrum was obtained in CDCl3 with the following results (δ in ppm, 250 MHz): δ=7.7–6.7 (m, 8H, Ar, CH═N); δ=6.6 (d, 2H, 2-H, 6-H of p-Ph); δ=4.4–3.6 (m, 2H, NCH2CH); δ=3.6–3.0 (m, 5H, CH2CH3, CH2CHCH2); δ=2.75 (m, 1H, ABX, cis-HA of CH2O); δ=2.55 (m, ABX, trans-HB of CH2O); δ=1.1 (t, J=7.0 Hz, 6H, CH3). An elemental analysis found the following weight percents of the elements: C, 74.45; H, 7.84; N, 12.72, which compares with the following calculated elemental weight percent for a compound with the formula C20H25N3O of: C, 74.27; H, 7.79; N, 12.99.

Workup

  1. customthe product was recrystallized from diethyl ether
  2. customrecrystallized from diethyl ether
  3. customA 1H-NMR spectrum was obtained in CDCl3 with the
  4. customfollowing results (δ in ppm, 250 MHz)

Sources & evidence

ORD record
ord-069148c0b05f4b968626e4d378ff94fa
Source dataset
uspto-grants-2006_07
Patent number
US07074532B2

Reaction notes

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