p-Toluenesulfonic acid → HCID 21310722, compound

HRID 583184Notes

Reaction equation

HRID 583184 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4](O)[C:3]=1[NH:12][C:13](=[O:15])[CH3:14].CC1C=CC(S(O)(=O)=O)=CC=1>CN(C1C=CN=CC=1)C.ClC1C=CC=C(Cl)C=1>[Br:1][C:2]1[C:3]2[N:12]=[C:13]([CH3:14])[O:15][C:4]=2[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 21310735HCID 21310735, compound

Product 1

HCID 21310722HCID 21310722, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 109431,3-DichlorobenzeneSolvent

Procedure

A solution of 1.15 g of N-(2-bromo-6-hydroxy-4-nitrophenyl)acetamide, 80 mg Tosic acid, 26 mg DMAP, in 25 mL 1,3-dichorobenzene was heated at 170° C. overnight. Reaction was then washed with satd. NaHCO3 and brine, dried over MgSO4, and conc. in vacuo. The product was purified on a silica gel column, eluting with 80% hexane/20% EtOAc. 910 mg of title compound was recovered.

Workup

  1. customReaction
  2. washwas then washed with satd
  3. dry with materialNaHCO3 and brine, dried over MgSO4
  4. customThe product was purified on a silica gel column
  5. washeluting with 80% hexane/20% EtOAc
  6. custom910 mg of title compound was recovered

Sources & evidence

ORD record
ord-0383566f01f54bab8e97adf17d980742
Source dataset
uspto-grants-1999_07
Patent number
US05929094

Reaction notes

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