Phosphorus pentachloride → {2-[Acetyl(2,6-dichlorophenyl)amino]phenyl}acetyl chloride

HRID 2164236Notes

Reaction equation

HRID 2164236 reaction equation
[C:1]([N:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]([OH:22])=O)[C:5]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:12])(=[O:3])[CH3:2].P(Cl)(Cl)(Cl)(Cl)[Cl:24]>C(OCC)C>[C:1]([N:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]([Cl:24])=[O:22])[C:5]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:12])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 20405977{2-[Acetyl(2,6-dichlorophenyl)amino]phenyl}acetic acid

Product 1

HCID 54434035{2-[Acetyl(2,6-dichlorophenyl)amino]phenyl}acetyl chloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-[N-Acetyl-N-(2,6-dichlorophenyl)amino]phenylacetic acid is reacted with phosphorus pentachloride in diethyl ether to obtain 2-[N-acetyl-N-(2,6-dichlorophenyl)amino]phenylacetic acid chloride. The acid chloride is then reacted with trimethyl phosphite under the conditions described in Example 2, thus producing 2-[N-acetyl-N-(2,6-dichlorophenyl)amino]phenyl-1-hydroxyethene-1-phosphonic acid dimethyl ester; this compound is converted, under the conditions of Example 1, with dimethyl phosphite into 2-[2-(2,6-dichlorophenylamino)phenyl]-1-hydroxyethane-1,1-bis(phosphonic acid dimethyl ester).

Sources & evidence

ORD record
ord-501e5aefd2014e60bf53fafcf5045dfa
Source dataset
uspto-grants-1985_03
Patent number
US04503049

Reaction notes

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