Benzylaniline → 1-octyl-2-phenyl-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide

HRID 2058891Notes

Reaction equation

HRID 2058891 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([P:23](Cl)(Cl)=[O:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C(Cl)Cl>[CH2:15]([P:23]1(=[O:24])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH2:1][N:8]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 66028BenzylanilineHCID 76541Octylphosphonic dichloride2×

Product 1

HCID 130374921-octyl-2-phenyl-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxideYield 5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure of Example 1 was employed utilizing N-benzylaniline and octyl phosphonic dichloride. The reaction of the dilithio compound and the octyl phosphonic dichloride was conducted at -65° C. The crude product produced as a result of the chromatographic separation was dissolved in methylene chloride and separated on a Woelm's neutral alumina column using ethyl acetate as the eluant to yield 1-octyl-2-phenyl-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide (1.1 g, 5% yield) as a pale yellow oil (nD =1.5502).

Workup

  1. customwas conducted at -65° C
  2. customThe crude product produced as
  3. customa result of the chromatographic separation
  4. customseparated on a Woelm's neutral alumina column

Sources & evidence

ORD record
ord-75f88e0661824ffb9c908ae1fff302d8
Source dataset
uspto-grants-1982_03
Patent number
US04319913

Reaction notes

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