Phenylphosphonic dichloride → HCID 13037499, compound

HRID 2058897Notes

Reaction equation

HRID 2058897 reaction equation
[C:1]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[C:13]1([P:19](Cl)(Cl)=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[C:13]1([P:19]2(=[O:20])[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[CH2:6][N:5]2[C:1]([CH3:4])([CH3:2])[CH3:3])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 69990Phenylphosphonic dichloride2×HCID 76908N-(1,1-Dimethylethyl)benzenemethanamine

Product 1

HCID 13037499HCID 13037499, compoundYield 16%

Procedure

The procedure of Example 1 was employed utilizing N-t-butyl-N-benzylamine and phenyl phosphonic dichloride. The reaction of the dilithio compound and the phenyl phosphonic dichloride was conducted at 0° 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-phenyl-2-(t-butyl)-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide (2.75 g, 16% yield) as a white solid having a melting point of 89°-91° 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 160° C.
  5. custom0.2 mm to yield a colorless oil

Sources & evidence

ORD record
ord-14bbab2faa8b4b2eb95e4b0b65e9e381
Source dataset
uspto-grants-1982_03
Patent number
US04319913

Reaction notes

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