4-Nitrophenol → 3-[2-(4-Methylphenylsulphonylamino)-ethyl]-phenoxyacetic acid benzylamide

HRID 1757480Notes

Reaction equation

HRID 1757480 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=2)[O:17][CH2:18][C:19]([OH:21])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.ClC1C=CC(S(NCCC2C=C(C=CC=2)OCCCC(O)=O)(=O)=O)=CC=1.C(C1NC=CN=1)(C1NC=CN=1)=O.C1C([N+]([O-])=O)=CC=C(O)C=1.[CH2:73]([NH2:80])[C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1>>[CH2:73]([NH:80][C:19](=[O:21])[CH2:18][O:17][C:16]1[CH:22]=[CH:23][CH:24]=[C:14]([CH2:13][CH2:12][NH:11][S:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)(=[O:9])=[O:10])[CH:15]=1)[C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1

Participants

6

Reactant 5

HCID 9804-NitrophenolHCID 7504BenzylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 138270173-[2-(4-Methylphenylsulphonylamino)-ethyl]-phenoxyacetic acidHCID 193881404-[3-[2-(4-Chlorophenylsulphonylamino)-ethyl]-phenoxy]butyric acid

Product 1

HCID 536881003-[2-(4-Methylphenylsulphonylamino)-ethyl]-phenoxyacetic acid benzylamide

Conditions

Temperature
40 °C

Procedure

To a 40° C. warm mixture of 10.0 g (28.6 mmol) 3-[2-(4-methylphenylsulphonylamino)-ethyl]-phenoxyacetic acid and 100 ml abs. THF one adds 4.64 g (28.6 mmol) carbonyl-bisimidazole and allows to react for 10 min. 0.4 g (28.6 mmol) p-nitrophenol are then added thereto. After 10 min. one adds thereto 3.1 g (28.6 mmol) benzylamine and stirs fortwo hrs. at 60° C. Subsequently, THF is distilled off, the residue mixed with ice and dil. HCl and shaken out with methylene chloride. One extracts the organic phase twice with NaHCO3 solution and once with water. After drying with MgSO4, it is evaporated and recrystallised (ethanol). Yield 10.2 g (81% of theory); m.p. 118°-120° C.

Workup

  1. customto react for 10 min
  2. additionAfter 10 min. one adds
  3. customat 60° C
  4. distillationSubsequently, THF is distilled off
  5. additionthe residue mixed with ice and dil. HCl
  6. dry with materialAfter drying with MgSO4, it
  7. customis evaporated
  8. customrecrystallised (ethanol)

Sources & evidence

ORD record
ord-5849e93686d4400fb7045372d3d7680f
Source dataset
uspto-grants-1995_08
Patent number
US05446065

Reaction notes

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