p-Toluenesulfonic acid → HCID 977867, compound

HRID 2243100Notes

Reaction equation

HRID 2243100 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](Cl)=[O:6].[NH2:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=1O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][C:14]3[CH:15]=[CH:16][C:17]([N+:19]([O-:21])=[O:20])=[CH:18][C:13]=3[N:12]=2)[CH:8]=[CH:9][C:10]=1[Cl:11]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 977867HCID 977867, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3,4-Dichlorobenzoyl chloride (4.6 g, 0.022 mol) is added to 2-amino-4-nitrophenol (3.4 g, 0.022 mol) in toluene (250 ml) and the mixture is refluxed for 24 hours. para-Toluenesulfonic acid (1.0 g) is added, the mixture is refluxed for 24 hours and cooled, and the product is filtered off. It is recrystallized from isopropyl ether. Yield: 6.8 g; IR (KBr): 3100, 1531, 1350 cm−1.

Workup

  1. temperaturethe mixture is refluxed for 24 hours
  2. temperaturethe mixture is refluxed for 24 hours
  3. temperaturecooled
  4. filtrationthe product is filtered off
  5. customIt is recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-6ce0ab23e218475a8d68c1468bbac277
Source dataset
uspto-grants-2010_03
Patent number
US07674809B2

Reaction notes

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