(2,4-Dichlorophenoxy)Acetic Acid → 2-(2,4-dichlorophenoxy)-N-(3-hydroxyphenyl)acetamide

HRID 1945399Notes

Reaction equation

HRID 1945399 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[NH2:14][C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1.F[P-](F)(F)(F)(F)F.[PH4+].C(N(CC)C(C)C)(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=1)=[O:8]

Participants

6

Reactant 4

HCID 1486(2,4-Dichlorophenoxy)Acetic AcidHCID 115683-AminophenolHCID 81531DiisopropylethylamineHCID 21584439Phosphonium hexafluorophosphate

Product 1

HCID 8366682-(2,4-dichlorophenoxy)-N-(3-hydroxyphenyl)acetamideYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the (2,4-dichloro-phenoxyacetic acid (600 mg, 2.71 mmol) and 3-amino-phenol (592 mg, 5.43 mmol) in DMF (20.0 mL) were added benzotriazol-1-yl-N-oxy-trispyrrolidino)-phosphonium hexafluorophosphate (PyBOP) (2.8 g, 5.43 mmol), and N,N-diisopropylethylamine (DIPEA) (0.95 ml, 5.43 mmol). The reaction mixture was stirred at room temperature overnight, and then partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4anh), and concentrated. Purification by silica gel column chromatography (n-Hexane:EtOAc:MeOH=10:3:1) gave 2-(2,4-Dichloro-phenoxy)-N-(3-hydroxy-phenyl)-acetamide as a white solid (837 mg, 99% yield)

Workup

  1. custompartitioned between ethyl acetate and brine
  2. customThe organic phase was dried (MgSO4anh)
  3. concentrationconcentrated
  4. customPurification by silica gel column chromatography (n-Hexane:EtOAc:MeOH=10:3:1)

Sources & evidence

ORD record
ord-b6d58ca94fb24d9e8d0677a351e8b2d2
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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