N-benzyl-4-methylaniline → 1-isopropyl-2-(4-methylphenyl)-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide

HRID 2058879Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH:16]([P:19](Cl)(Cl)=[O:20])([CH3:18])[CH3:17]>>[CH:16]([P:19]1(=[O:20])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][N:8]1[C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)([CH3:18])[CH3:17]

Participants

Reactant 2

HCID 79403N-benzyl-4-methylaniline

HCID 2793751Isopropylphosphonic dichloride

Product 1

HCID 130374801-isopropyl-2-(4-methylphenyl)-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxideYield 32%

Procedure

The procedure of Example 1 was employed utilizing N-(4-methylphenyl)-N-benzylamine and isopropyl phosphonic dichloride to yield 1-isopropyl-2-(4-methylphenyl)-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide (5.4 g, 32% yield) as white crystals having a melting point of 135°-137° C. and the following analysis:

Sources & evidence

ORD record: ord-ec508beab6a44aa4a85289ccba0faa51
Source dataset: uspto-grants-1982_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04319913

Reaction notes

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