Methane → HCID 15347129, compound

HRID 1604082Notes

Reaction equation

HRID 1604082 reaction equation
[OH:1][CH2:2][CH2:3][N:4](CCO)[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([N+:12]([O-])=O)[CH:6]=1.OCCNC1C=CC(O)=C([N+]([O-])=O)C=1.C1OC1.C.NC1C=CC(O)=C([N+]([O-])=O)C=1>COCCOC.O>[OH:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([NH2:12])[CH:6]=1

Participants

8

Reactant 5

HCID 297MethaneHCID 6354Ethylene Oxide2×HCID 34174194-Amino-2-NitrophenolHCID 153471284-[(2-Hydroxyethyl)amino]-2-nitrophenolHCID 19607167HCID 19607167, compound

Product 1

HCID 15347129HCID 15347129, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
60 °C

Procedure

Preparation of 4-[bis(2-hydroxyethyl)-amino]-2-nitrophenol by ethoxylation (B5.c): 397 g (2 mol) 4-(2-hydroxyethylamino)-2-nitrophenol is added to a mixture of 1.6 liters of water and 1.1 liters of 1,2-dimethoxyethane. The system is closed with a bubble counter and heated with stirring to 60° C. Ethylene oxide is conducted into this solution so that no ethylene oxide escapes through the bubble counter. After 5 hours the temperature is increased to 85° C., 9.2 g activated charcoal and 4.6 g Celite are added, and stirring is continued for 15 minutes. Then the mixture is filtered with suction. The residue is washed with 100 ml of 1,2-dimethoxyethane/water (1:1 v/v). 500 ml of 1,2-dimethoxyethane is distilled off the solution. The product which precipitates is filtered off with suction and dried. (This product is obtained starting from 4-amino-2-nitrophenol according to this procedure.)

Workup

  1. customThe system is closed with a bubble counter
  2. temperatureheated
  3. temperatureAfter 5 hours the temperature is increased to 85° C.
  4. additionare added
  5. stirringstirring
  6. filtrationThen the mixture is filtered with suction
  7. washThe residue is washed with 100 ml of 1,2-dimethoxyethane/water (1:1 v/v)
  8. distillation500 ml of 1,2-dimethoxyethane is distilled off the solution
  9. customThe product which precipitates
  10. filtrationis filtered off with suction
  11. customdried
  12. custom(This product is obtained

Sources & evidence

ORD record
ord-bce5c6c126e74819acda4df03bd1d344
Source dataset
uspto-grants-1999_11
Patent number
US05990355

Reaction notes

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