Oxalic Acid → HCID 24991929, compound

HRID 557471Notes

Reaction equation

HRID 557471 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[O:5][CH2:6][CH2:7][NH2:8].[O:13]1[CH2:30][CH:14]1[CH2:15][O:16][C:17]1[C:29]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][C:21]=2[CH:20]=[CH:19][CH:18]=1.[C:31]([OH:36])(=[O:35])[C:32]([OH:34])=[O:33]>ClC1C=CC=CC=1>[C:31]([OH:36])(=[O:35])[C:32]([OH:34])=[O:33].[CH:20]1[C:21]2[NH:22][C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:29]=2[C:17]([O:16][CH2:15][CH:14]([OH:13])[CH2:30][NH:8][CH2:7][CH2:6][O:5][C:4]2[CH:9]=[CH:10][CH:11]=[CH:12][C:3]=2[O:2][CH3:1])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 17130052-(2-Methoxyphenoxy)ethyl amineHCID 50207104-Oxiranylmethoxy-9H-carbazole

Product 1

HCID 24991929HCID 24991929, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
125 °C

Procedure

146.4 g (0.875 moles, 2.1 mol equivalents) of 2-(2-methoxy phenoxy)ethylamine is dissolved in 500 ml of monochlorobenzene and the temperature is raised 125° C. under stirring. 100 g (0.42 moles) of 4-(2,3-epoxy propoxy)carbazole is slowly added in lots over 1 hr at reflux temperature. Reflux is then carried on for two hrs. Distilled of the monochlorobenzene under vacuum followed by cooling of the reaction mass to 50-60° C. 1000 ml isopropyl acetate is charged followed by the addition of 1000 ml DM water. pH of reaction mass is adjusted to 2.0-2.5 with 10% oxalic acid solution at 45° C.-50° C. Stirred for one hr at 45° C.-50° C., the reaction mass is cooled to room temperature and maintained for two hrs. The material is filtered washed with isopropyl acetate and water mixture and then dried at 50° C.-60° C.

Workup

  1. temperatureat reflux temperature
  2. temperatureReflux
  3. customis then carried on for two hrs
  4. distillationDistilled of the monochlorobenzene under vacuum
  5. temperatureby cooling of the reaction mass to 50-60° C
  6. addition1000 ml isopropyl acetate is charged
  7. additionfollowed by the addition of 1000 ml DM water
  8. custompH of reaction mass
  9. stirringStirred for one hr at 45° C.-50° C.
  10. temperaturethe reaction mass is cooled to room temperature
  11. temperaturemaintained for two hrs
  12. filtrationThe material is filtered
  13. washwashed with isopropyl acetate and water mixture
  14. customdried at 50° C.-60° C.

Sources & evidence

ORD record
ord-36fd75c46114462b85cb5ef2a8828555
Source dataset
uspto-grants-2011_11
Patent number
US08058453B2

Reaction notes

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