Aniline → HCID 53937757, compound

HRID 1734959Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8](Cl)(=[O:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>>[C:2]1([NH:1][C:8](=[O:15])[CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 6115Aniline

HCID 17313Heptanoyl chloride

Product 1

HCID 53937757HCID 53937757, compoundYield 94%

Procedure

The procedure described in Example 1 is repeated, but in section a) aniline is used in place of n-pentylamine and n-heptanoyl chloride is used in place of caproyl chloride. N-Phenyl-n-heptenamide (m.p. 50° C.) is obtained in 94% yield. This is reacted with PCl5 as in Example 1, section b), and gives in quantitative yield N-phenyl-heptaneiminoyl chloride as a yellowish oil which is converted according to section c) into the desired product and purified by chromatography on silica gel in hexane/ether=1:1. M.p. 83°-84° C. UV (EtOH): 320 nm (ε=19502).

Sources & evidence

ORD record: ord-ae9f9310eacc48fe9fab4e07a49eee1f
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05536453

Reaction notes

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