P-Phenylenediamine → HCID 18510729, compound

HRID 2219081Notes

Reaction equation

HRID 2219081 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:16]1[CH:21]=[CH:20][C:19]([S:22]([C:25]([F:28])([F:27])[F:26])(=[O:24])=[O:23])=[CH:18][CH:17]=1>O>[F:27][C:25]([F:26])([F:28])[S:22]([C:19]1[CH:20]=[CH:21][C:16]([NH:7][C:4]2[CH:5]=[CH:6][C:1]([NH2:8])=[CH:2][CH:3]=2)=[CH:17][CH:18]=1)(=[O:23])=[O:24]

Participants

5

Reactant 3

HCID 7814P-PhenylenediamineHCID 11430Potassium CarbonateHCID 7033241-Chloro-4-(trifluoromethylsulfonyl)benzene

Product 1

HCID 18510729HCID 18510729, compoundYield 0%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 0,277 mol of 1,4-benzenediamine, 0,017 mol of methyl 2-hydroxy benzoate and 10 grams of potassium carbonate is stirred for 1 hour at 190° C. Then there are added 0,049 mol of 1-chloro-4-(trifluoromethylsulfonyl)benzene and stirring at 190° C. is continued for 3 hours. The reaction mixture is cooled and stirred in 2000 ml of water. The precipitated product is filtered off, washed with water, dried and crystallized from a mixture of ethanol and water, yielding 2.3 grams of N-[4-(trifluoromethylsulfonyl)phenyl]-1,4-benzenediamine. (interm. 6)

Workup

  1. stirringstirring at 190° C.
  2. waitis continued for 3 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationThe precipitated product is filtered off
  5. washwashed with water
  6. customdried
  7. customcrystallized from a mixture of ethanol and water

Sources & evidence

ORD record
ord-0bae3cb542ee460a8a5b6396d9276b83
Source dataset
uspto-grants-2008_08
Patent number
US07414048B2

Reaction notes

Loading…