Water → HCID 24991929, compound

HRID 557470Notes

Reaction equation

HRID 557470 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.O.[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34]>ClC1C=CC=CC=1>[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34].[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

6

Reactant 4

HCID 962WaterHCID 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

174 g (1.04 moles, 2.5 mol equivalents) of 2-(2-methoxy phenoxy)ethylamine is dissolved in 500 ml of monochlorobenzene. The temperature is raised to 125° C. under stirring. 100 g (0.42 moles) of 4-(2,3-epoxy propoxy)carbazole is slowly added in five lots during 1 hr at reflux temperature. Refluxing is then carried on for two hrs. The reaction is monitored to completion by thin layer chromatography and then cooled to 90° C. 500 ml water is then charged followed by cooling to 70° C. The pH of reaction mass is adjusted to 2.5-2.7 with 10% oxalic acid solution at 60° C.-70° C. Stirring is done for one hr at 60° C.-70° C. The reaction mass is cooled to room temp and maintained for two hrs. The material is filtered and washed with water and dried at 50° C.-60° C.

Workup

  1. temperatureat reflux temperature
  2. temperatureRefluxing
  3. customis then carried on for two hrs
  4. temperaturecooled to 90° C
  5. temperatureby cooling to 70° C
  6. customThe pH of reaction mass
  7. stirringStirring
  8. temperatureThe reaction mass is cooled to room temp
  9. temperaturemaintained for two hrs
  10. filtrationThe material is filtered
  11. washwashed with water
  12. customdried at 50° C.-60° C.

Sources & evidence

ORD record
ord-6cee6d06934c4ed0b38cee79c46c9dff
Source dataset
uspto-grants-2011_11
Patent number
US08058453B2

Reaction notes

Loading…