(4-Nitrophenyl)acetic acid → HCID 2282537, compound

HRID 393508Notes

Reaction equation

HRID 393508 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25](O)=[O:26])=[CH:20][CH:19]=1)([O-:17])=[O:16].OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1>[N+:15]([C:18]1[CH:19]=[CH:20][C:21]([CH2:24][C:25]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([NH:7][C:4]3[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=3)=[CH:9][CH:10]=2)=[O:26])=[CH:22][CH:23]=1)([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 4661(4-Nitrophenyl)acetic acidHCID 7564N-Phenyl-p-phenylenediamineHCID 10868DicyclohexylcarbodiimideHCID 178418300HCID 178418300, compound

Product 1

HCID 2282537HCID 2282537, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.84 g (10 mmol) of 4-aminodiphenylamine, 1.81 g (10 mmol) of 4-nitrophenylacetic acid and 1.48 g (11 mmol) of hydroxybenzotriazole in 40 ml of THF are dissolved successively in a 100 ml flask. Then 2.27 g (11 mmol) of 1,3-dicyclohexylcarbodiimide (DCC) is added and the reaction mixture is agitated for 15 hours. A precipitate of dicyclohexylurea (DCU) forms which is filtered and rinsed with 100 ml of ethyl acetate. The filtrate is then washed successively with 50 ml of a saturated solution of Na2CO3, 50 ml of water, 50 ml of a molar solution of HCl and finally 2×50 ml of salt water. The organic phase is dried over magnesium sulphate, filtered and concentrated under vacuum. The residue is purified rapidly on a silica gel column (eluent: heptane/ethyl acetate 1/1). The purest fractions are collected and evaporated under vacuum in order to produce a brown powder. The product is used as it is in the following stage.

Workup

  1. filtrationA precipitate of dicyclohexylurea (DCU) forms which is filtered
  2. washrinsed with 100 ml of ethyl acetate
  3. washThe filtrate is then washed successively with 50 ml of a saturated solution of Na2CO3, 50 ml of water, 50 ml of a molar solution of HCl and finally 2×50 ml of salt water
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified rapidly on a silica gel column (eluent: heptane/ethyl acetate 1/1)
  8. customThe purest fractions are collected
  9. customevaporated under vacuum in order
  10. customto produce a brown powder

Sources & evidence

ORD record
ord-caa6da1a36c4410aa685e8c543e8d252
Source dataset
uspto-grants-2004_10
Patent number
US06809090B2

Reaction notes

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