Methanol → HCID 18993051, compound

HRID 375537Notes

Reaction equation

HRID 375537 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:8].[Cl:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.CO>O.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]2[NH:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 7243O-PhenylenediamineHCID 14146341HCID 14146341, compound

Product 1

HCID 18993051HCID 18993051, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 165397Cupric acetate monohydrateCatalystHCID 962WaterSolvent

Procedure

A mixture of copper (II) acetate monohydrate (7.76 g), 1,2-diaminobenzene (2.10 g), 4-(4-chlorobutoxy]benzaldehyde (Step A) (5.0 g) is slowly heated to reflux in water (10 mL) and methanol (100 mL) and stirred at reflux for 1 hour. The mixture is cooled and a brown precipitate filtered off. The precipitate is suspended in methanol (100 mL) and hydrogen sulfide bubbled through for 30 minutes followed by nitrogen. The mixture is heated to reflux, cooled and filtered. All the filtrates are combined and 0.880 ammonium hydroxide added until just basic. The filtrates are diluted with an equal volume of water and the resulting pale-grey precipitate collected. The precipitate is recrystallized from methanol/water to give 3.8 g of the title compound.

Workup

  1. temperatureis slowly heated
  2. temperatureat reflux for 1 hour
  3. temperatureThe mixture is cooled
  4. filtrationa brown precipitate filtered off
  5. customhydrogen sulfide bubbled through for 30 minutes
  6. temperatureThe mixture is heated
  7. temperatureto reflux
  8. temperaturecooled
  9. filtrationfiltered
  10. addition0.880 ammonium hydroxide added until just basic
  11. additionThe filtrates are diluted with an equal volume of water
  12. customthe resulting pale-grey precipitate collected
  13. customThe precipitate is recrystallized from methanol/water

Sources & evidence

ORD record
ord-365a83eeb47148309f09a31af0b046da
Source dataset
uspto-grants-1996_01
Patent number
US05486517

Reaction notes

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