Water → HCID 13910811, compound

HRID 979073Notes

Reaction equation

HRID 979073 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([NH2:18])[CH:12]=2)[CH:5]=[CH:6][C:7]=1[OH:8].C(=O)(O)[O-].[Na+].O.Cl[CH2:26][C:27](Cl)=[O:28].[CH3:30][C:31](CC(C)C)=[O:32]>>[O:8]1[C:7]2[CH:6]=[CH:5][C:4]([CH2:9][CH2:10][C:11]3[CH:16]=[CH:15][C:14]4[O:17][CH2:30][C:31](=[O:32])[NH:18][C:13]=4[CH:12]=3)=[CH:3][C:2]=2[NH:1][C:27](=[O:28])[CH2:26]1

Participants

6

Reactant 5

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 7909Methyl Isobutyl KetoneHCID 516892Sodium BicarbonateHCID 194382834,4′-(1,2-Ethanediyl)bis[2-aminophenol]

Product 1

HCID 13910811HCID 13910811, compound

Procedure

To 3.0 g (0.0123 mole) of 1,2 bis(3-amino-4-hydroxyphenyl)ethane in 25 ml of isobutyl methyl ketone was added 5.0 g (0.06 mole) sodium bicarbonate and 25 ml of water. The mixture was cooled in an ice-bath and 1.4 g (0.012 mole) of chloroacetyl chloride was added dropwise over 15 minutes. After coming to room temperature, the mixture was refluxed for 4 hours. On cooling, the solid was filtered off and washed with acetone. The precipitate was suspended in acetone, refluxed for 15 minutes and cooled. On filtration, there was obtained 2.3 g of a beige solid.

Workup

  1. temperatureThe mixture was cooled in an ice-bath
  2. customAfter coming to room temperature
  3. temperaturethe mixture was refluxed for 4 hours
  4. temperatureOn cooling
  5. filtrationthe solid was filtered off
  6. washwashed with acetone
  7. temperaturerefluxed for 15 minutes
  8. temperaturecooled
  9. filtrationOn filtration

Sources & evidence

ORD record
ord-129969ccb0f44f779065fe8f369c9b2a
Source dataset
uspto-grants-1987_05
Patent number
US04666909

Reaction notes

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