Water → HCID 21074069, compound

HRID 1593943Notes

Reaction equation

HRID 1593943 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:14]1([NH2:21])[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>[Cu].C(O)(=O)C>[NH2:20][C:16]1[CH:15]=[C:14]([NH:21][C:2]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7935M-PhenylenediamineHCID 11430Potassium CarbonateHCID 172872-Chloro-5-nitrobenzoic acid

Product 1

HCID 21074069HCID 21074069, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-chloro-5-nitrobenzoic acid 16 (150.0 g, 744 mmol), 1,3-phenylenediamine 17 (150.0 g, 1.387 mol), anhydrous potassium carbonate (309.0 g, 2.236 mol ), copper powder (2.0 g, 31.5 mmol), cupric sulfate (10 mg) and water (2.0 L) was heated to reflux with stirring for 6.25 hr under argon. It was then allowed to stand overnight at room temperature. Glacial acetic acid was added to the reaction mixture with stirring until pH 5 and the flask cooled in ice water. The mustard yellow solid was collected, washed with ice-cold water (3×100 mL), and redissolved in hot dilute ammonia (300 mL 0.88 s.g. ammonia and 2.7 L water). Charcoal (2.0 g) was added, the mixture refluxed briefly, and then filtered through a fluted paper. On cooling to room temperature the mixture was acidified to pH 5 by adding glacial acetic acid and the flask cooled in ice-water. The product was collected and washed with ice-cold water (2×100 mL) followed by ice-cold ethanol (2×100 mL), dry ether (2×100 mL) and finally hexane (100 mL). The product was dried over P2O5 under vacuum to yield the product AR-ACO-06 (155.10 g, 76%) as brown solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. waitto stand overnight at room temperature
  4. stirringwith stirring until pH 5
  5. customThe mustard yellow solid was collected
  6. washwashed with ice-cold water (3×100 mL)
  7. dissolutionredissolved in hot dilute ammonia (300 mL 0.88 s.g. ammonia and 2.7 L water)
  8. additionCharcoal (2.0 g) was added
  9. temperaturethe mixture refluxed briefly
  10. filtrationfiltered through a fluted paper
  11. additionby adding glacial acetic acid
  12. temperaturethe flask cooled in ice-water
  13. customThe product was collected
  14. washwashed with ice-cold water (2×100 mL)
  15. dry with materialThe product was dried over P2O5 under vacuum
  16. customto yield the product AR-ACO-06 (155.10 g, 76%) as brown solid

Sources & evidence

ORD record
ord-ef3fa917b2914925bdb1194d2f1d9504
Source dataset
uspto-grants-2007_11
Patent number
US07300930B2

Reaction notes

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