Diphenyl-o-tolylphosphine → [(2-Methylphenyl)diphenylphosphoranylidene]carbamic acid, ethyl ester

HRID 329918Notes

Reaction equation

HRID 329918 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[P:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:21]([N:26]=[N+]=[N-])(=[O:25])[O:22][CH2:23][CH3:24]>CCOCC>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[P:8](=[N:26][C:21](=[O:25])[O:22][CH2:23][CH3:24])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 80040Diphenyl-o-tolylphosphineHCID 11819065Ethyl azidoformate

Product 1

HCID 14280265[(2-Methylphenyl)diphenylphosphoranylidene]carbamic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1.0 g of (2-methylphenyl)diphenylphosphine in 30 ml of ether was treated with 4 ml of 1M ethyl carbonazidate in ether. The mixture was allowed to stand 48 hours, then repeatedly concentrated and finally treated with fresh ether and refrigerated, giving 930 mg of the desired compound, mp 113°-114° C.

Workup

  1. concentrationrepeatedly concentrated
  2. additionfinally treated with fresh ether

Sources & evidence

ORD record
ord-073b4472a9e944b69d6799e1fda16a31
Source dataset
uspto-grants-1990_01
Patent number
US04894368

Reaction notes

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