Benzylaniline → 1-(4-phenoxyphenyl)-2-phenyl-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide

HRID 2058896Notes

Reaction equation

HRID 2058896 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.[O:15]([C:22]1[CH:27]=[CH:26][C:25]([P:28](Cl)(Cl)=[O:29])=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[O:15]([C:22]1[CH:27]=[CH:26][C:25]([P:28]2(=[O:29])[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH2:1][N:8]2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:24][CH:23]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 66028BenzylanilineHCID 12670623(4-Phenoxyphenyl)phosphonic dichloride2×

Product 1

HCID 130374981-(4-phenoxyphenyl)-2-phenyl-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide

Procedure

The procedure of Example 1 was employed utilizing N-benzylaniline and 4-phenoxyphenyl phosphonic dichloride. The reaction of the dilithio compound and the 4-phenoxyphenyl phosphonic dichloride was conducted at 0° C. The crude product produced as a result of the chromatographic separation was distilled at 140° C. and the resulting residue was crystallilzed from diethyl ether to yield 1-(4-phenoxyphenyl)-2-phenyl-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide as beige needles. A second crop was obtained to give a total yield of 0.75 g, 3% yield of 1-(4-phenoxyphenyl)-2-phenyl-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide having a melting point of 207°-208° C. and the following analysis:

Workup

  1. customwas conducted at 0° C
  2. customThe crude product produced as
  3. customa result of the chromatographic separation
  4. distillationwas distilled at 140° C.

Sources & evidence

ORD record
ord-fd1a5aff49364856a5d62aee913dd532
Source dataset
uspto-grants-1982_03
Patent number
US04319913

Reaction notes

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