Water → HCID 67866603, compound

HRID 1030466Notes

Reaction equation

HRID 1030466 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][CH2:21]Cl)=[C:6]([CH:12]=1)[O:7][CH2:8][CH2:9][NH:10][CH3:11].N1C=CC=CC=1.O.[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34]>CN1CCCC1=O>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH2:20][CH2:21][N:10]([CH3:11])[CH2:9][CH2:8][O:7][C:6]=2[CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 444266Maleic AcidHCID 19820420HCID 19820420, compound

Product 1

HCID 67866603HCID 67866603, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

A solution of 9.9 g of 2-[5-chloro-2-[(2-chloroethyl)phenoxy]phenoxy]-N-methyl-ethylamine dissolved in 500 ml of N-methyl-2-pyrrolidone was slowly added to a mixture of 1 1 of N-methyl-2-pyrrolidone and 500 ml of pyridine at 85° C. and stirred overnight at this temperature. Water was added, the mixture was extracted with diethyl ether and the ether layer was washed with water and dried over sodium sulphate. The organic solution was evaporated to dryness and the residue was crystallized from dichloromethane-diethyl ether after addition of 1 eq of maleic acid to obtain 2.3 g (28%) of 3-chloro-7,8,9,10-tetrahydro-8-methyl-6H-dibenzo[b,j][1,4,7]dioxaazacycloundecine (Z)-2-butenedioate (1:1). Mp 145-157° C.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washthe ether layer was washed with water
  3. dry with materialdried over sodium sulphate
  4. customThe organic solution was evaporated to dryness
  5. customthe residue was crystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-c15743af7e954f77a92949d9a6c025cb
Source dataset
uspto-grants-1992_04
Patent number
US05106839

Reaction notes

Loading…