N-(3-Methylphenyl)benzenemethanamine → 1-isopropyl-2-(3-methylphenyl)-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide

HRID 2058882

Reaction equation

HRID 2058882 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=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:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=1)([CH3:18])[CH3:17]

Participants

3

Reactant 2

HCID 222281N-(3-Methylphenyl)benzenemethanamineHCID 2793751Isopropylphosphonic dichloride

Product 1

HCID 130374841-isopropyl-2-(3-methylphenyl)-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxideYield 20%

Procedure

The procedure of Example 1 was employed utilizing N-(3-methylphenyl)-N-benzylamine and isopropyl phosphonic dichloride. The crude product produced as a result of the chromatographic separation was distilled at 150° C. and 0.8 mm to yield a pale yellow glass. The yellow glass was crystallized from methylcyclohexane to yield 1-isopropyl-2-(3-methylphenyl)-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide (3.5 g, 20% yield) as a white crystalline solid having a melting point of 112°-113° C. and the following analysis:

Workup

  1. customThe crude product produced as
  2. customa result of the chromatographic separation
  3. distillationwas distilled at 150° C.
  4. custom0.8 mm to yield a pale yellow glass
  5. customThe yellow glass was crystallized from methylcyclohexane

Sources & evidence

ORD record
ord-18d468e7766343a8899d88ab27001809
Source dataset
uspto-grants-1982_03
Patent number
US04319913

Linked notes

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