Dibenzylamine → 1-isopropyl-2-phenylmethyl-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide

HRID 2058892Notes

Reaction equation

HRID 2058892 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[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[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:18])[CH3:17]

Participants

3

Reactant 2

HCID 7656DibenzylamineHCID 2793751Isopropylphosphonic dichloride2×

Product 1

HCID 130374931-isopropyl-2-phenylmethyl-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxideYield 12%

Procedure

The procedure of Example 1 was employed utilizing dibenzylamine and isopropyl phosphonic dichloride. The reaction of the dilithio compound and the isopropyl phosphonic dichloride was conducted at -65° C. The crude product produced as a result of the chromatographic separation was distilled at 160° C. and 0.2 mm to yield a colorless oil. The colorless oil was slurried in petroleum ether to yield 1-isopropyl-2-phenylmethyl-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide (1.15 g, 12% yield) as a colorless solid having a melting point of 145°-147° C. and the following analysis:

Workup

  1. customwas conducted at -65° C
  2. customThe crude product produced as
  3. customa result of the chromatographic separation
  4. distillationwas distilled at 160° C.
  5. custom0.2 mm to yield a colorless oil

Sources & evidence

ORD record
ord-77b52decd2c446a7b69472a6ad93161b
Source dataset
uspto-grants-1982_03
Patent number
US04319913

Reaction notes

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