Water → HCID 68027740, compound

HRID 926657

Reaction equation

HRID 926657 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:12])[C:9](O)=[O:10])=[CH:4][CH:3]=1.[C:13]1([NH2:20])[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1.[OH2:21]>ClC1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:12])[C:9]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([NH:20][C:9](=[O:10])[CH:8]([C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)[OH:12])=[CH:14][CH:15]=2)=[O:21])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7814P-PhenylenediamineHCID 97930p-Bromomandelic acid

Product 1

HCID 68027740HCID 68027740, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

In a 250 cm3 flask fitted with a consender and a reverse Dean-Stark apparatus, the (4-bromo-phenyl)-hydroxy-acetic acid (25.00 g, 108.2 mmol) and 1,4-phenylenediamine (3.900 g, 36.07 mmol) are dissolved in chlorobenzene (100 cm3). The reaction mixture is heated to 132° C. while the generated water is distilled off the using the reverse Dean-Stark apparatus. After 21 hours, the reaction mixture is cooled down, the precipitate is filtered off and washed with methanol to yield the product (18.21 g, Yield: 95%). NMR (1H, 300 MHz, CDCl3): δ 9.90 (br, 2H); 7.59 (s, 4H); 7.56 (d, J=8.5 Hz, 4H); 7.45 (d, J=8.5 Hz, 4H); 6.53 (d, J=4.7 Hz, 2H), 5.08 (d, J=4.7 Hz, 2H).

Workup

  1. customIn a 250 cm3 flask fitted with a consender
  2. distillationis distilled off the using the reverse Dean-Stark apparatus
  3. temperaturethe reaction mixture is cooled down
  4. filtrationthe precipitate is filtered off
  5. washwashed with methanol

Sources & evidence

ORD record
ord-9494d1c9e7034ca39eb730abbeb12e6a
Source dataset
uspto-grants-2016_03
Patent number
US09287504B2

Linked notes

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