Acetoacetanilide → HCID 22959395, compound

HRID 2303737Notes

Reaction equation

HRID 2303737 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH2:11][CH2:12][N:13]=2)=[CH:5][CH:4]=1.[C:14](NC1C=CC=CC=1)(=[O:19])[CH2:15][C:16]([CH3:18])=[O:17]>>[CH3:1][N:2]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][CH2:11][CH2:12][N:13]=2)=[CH:7][CH:8]=1)[C:14](=[O:19])[CH2:15][C:16]([CH3:18])=[O:17]

Participants

3

Reactant 2

HCID 7592AcetoacetanilideHCID 18461942HCID 18461942, compound

Product 1

HCID 22959395HCID 22959395, compound

Procedure

This compound was prepared by treating 4-aminobenzonitrile with a slight excess, on a molar equivalents basis, of methyl iodide in tetrahydrofuran solvent for 4 hrs at room temperature. Removal of the THF and other volatiles, followed by recrystallization, gave a 76% yield of 4-(N-methyl)aminobenzonitrile, mp 85-87° C. Using Example 1 procedure, the aforesaid substituted nitrile was treated with ethanolamine to obtain a 70% yield of 2-[4-(N-methyl)aminophenyl]oxazoline, mp 145-147° C. Following the Example 6 procedure, the aforesaid compound was treated with TDO to form the oxazoline shown below, having a methyl group attached to the nitrogen in the acetoacetanilide segment. The product was recrystallized from ethyl acetate, mp 102-105° C. Elemental analysis, FT-IR, exhibiting 1726 (C—O) and 1635 (—C═N—) cm−1 absorptions, and with 1H NMR confirmed the below drawn structure.

Workup

  1. additionthe aforesaid compound was treated with TDO
  2. customThe product was recrystallized from ethyl acetate, mp 102-105° C

Sources & evidence

ORD record
ord-34dcc75953264d8f9e383e177fac18b7
Source dataset
uspto-grants-2002_08
Patent number
US06433116B1

Reaction notes

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