Ammonia → 4-(4,5-dihydro-1,3-oxazol-2-yl)aniline

HRID 1978142Notes

Reaction equation

HRID 1978142 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.N[CH2:11][CH2:12][OH:13].N>C([O-])(=O)C.[Zn+2].C([O-])(=O)C.C1(C)C(C)=CC=CC=1>[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]2[O:13][CH2:12][CH2:11][N:7]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 700EthanolamineHCID 133964-Aminobenzonitrile

Product 1

HCID 4239374-(4,5-dihydro-1,3-oxazol-2-yl)anilineYield 82%

Reagents, catalysts & solvents 2

HCID 11192Zinc AcetateCatalystHCID 7237O-XyleneSolvent

Procedure

Using known procedures for the synthesis of cyclic imino ethers from nitriles (18,26), 4-aminobenzonitrile was treated with an excess of 2-aminoethanol (1 part nitrile/2 parts aminoalcohol) in refluxing xylene, with 3.5 wt. % zinc acetate catalyst, with all under a slow nitrogen stream. The solution was heated until no NH3 was detected in the off gas. After removal of the xylene, the crude solid product was obtained in high yield. The crude product was recrystallized from acetonitrile to obtain an 82% yield of white, crystalline 4-APOXO having mp 163-165° C., reported 158-160° C. The structure of the monomer was confirmed by FT-IR and 1H NMR. Structure of 4-APOXO is as follows:

Workup

  1. customAfter removal of the xylene
  2. customthe crude solid product was obtained in high yield
  3. customThe crude product was recrystallized from acetonitrile
  4. customto obtain an 82% yield of white, crystalline 4-APOXO
  5. customreported 158-160° C

Sources & evidence

ORD record
ord-ff8111053a0249c0ad6bf6e20e6e28a9
Source dataset
uspto-grants-2001_05
Patent number
US06235901B1

Reaction notes

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