HCID 19838166, compound → HCID 22750172, compound

HRID 2164123Notes

Reaction equation

HRID 2164123 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:23][CH2:24][NH:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:33]([C:37]1[CH:46]=[CH:45][C:40]([O:41][CH2:42][CH2:43][Cl:44])=[CH:39][CH:38]=1)(=[O:36])(=[O:35])[NH2:34]>C1(C)C(C)=CC=CC=1>[ClH:44].[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:23][CH2:24][N:25]([CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:43][CH2:42][O:41][C:40]2[CH:39]=[CH:38][C:37]([S:33](=[O:36])(=[O:35])[NH2:34])=[CH:46][CH:45]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 19838166HCID 19838166, compoundHCID 221651544-(2-Chloroethoxy)benzene-1-sulfonamide

Product 1

HCID 22750172HCID 22750172, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of N-2-(3,4-dibenzyloxyphenyl)ethyl benzylamine (13.6 g.), 2-(4-sulfamoylphenoxy)ethyl chloride (4.8 g.) and dry xylene (50 ml.) was boiled under reflux for 12 hours. The solution was cooled and the precipitated solid removed by filtration, the filtrate then being evaporated in vacuo to dryness and taken up into diethyl ether. Insoluble material was removed from the ethereal solution by filtration, and the filtrate treated with ethereal hydrogen chloride, which resulted in the precipitation of a yellow solid. The latter was collected by filtration and recrystallized from a methanol/isopropanol mixture giving N-[2-(3,4-dibenzyloxyphenyl)ethyl]-N-[2-(4-sulfamoylphenoxy)ethyl] benzylamine hydrochloride (5.8 g.), m.p. 178°-181° C.

Workup

  1. temperatureunder reflux for 12 hours
  2. temperatureThe solution was cooled
  3. customthe precipitated solid removed by filtration
  4. customthe filtrate then being evaporated in vacuo to dryness
  5. customInsoluble material was removed from the ethereal solution by filtration
  6. additionthe filtrate treated with ethereal hydrogen chloride, which
  7. customresulted in the precipitation of a yellow solid
  8. filtrationThe latter was collected by filtration
  9. customrecrystallized from a methanol/isopropanol mixture

Sources & evidence

ORD record
ord-682b9f3fbd1d49ac8d822927cb86d2f4
Source dataset
uspto-grants-1979_01
Patent number
US04137328

Reaction notes

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