4-Aminophenol → 3,4-dichloro-N-(4-hydroxyphenyl)benzamide

HRID 1927716Notes

Reaction equation

HRID 1927716 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.N1C=CC=CC=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[Cl:25])[C:19](Cl)=[O:20]>CN(C=O)C.C(OCC)(=O)C.Cl>[Cl:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[Cl:25])[C:19]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1)=[O:20]

Participants

7

Reactant 3

HCID 4034-AminophenolHCID 1049PyridineHCID 76403Benzoyl chloride, 3,4-dichloro-

Product 1

HCID 9768083,4-dichloro-N-(4-hydroxyphenyl)benzamideYield 38%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-Aminophenol (1.9 g, 17 mmol) was diluted with DMF (40 mL) followed by the addition of pyridine (0.978) (1.4 mL, 17 mmol) and 3,4-dichlorobenzoyl chloride (3.0 g, 14 mmol) in 5 mL of DMF. After stirring for 12 hours, the reaction mixture was diluted with ethyl acetate and 2N HCl. The aqueous layer was extracted once with ethyl acetate. The organics were combined, washed with water, brine, dried over MgSO4, filtered and concentrated onto silica gel. The material was purified using a biotage 40M column eluting with hexanes:ethyl acetate (9:1) using 2 L and then (60:40) 1 L to yield 3,4-dichloro-N-(4-hydroxyphenyl)-benzamide (1.5 g, 37% yield) as a white solid.

Workup

  1. extractionThe aqueous layer was extracted once with ethyl acetate
  2. washwashed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated onto silica gel
  6. customThe material was purified
  7. washeluting with hexanes:ethyl acetate (9:1)

Sources & evidence

ORD record
ord-39d3dff4032a4ed8ad3f3ff6d887d579
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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