Epichlorohydrin → HCID 21480268, compound

HRID 1490016Notes

Reaction equation

HRID 1490016 reaction equation
[OH:1][C:2]1[CH:52]=[CH:51][C:5]([CH2:6][CH:7]2[CH2:18][N:17]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15][N:14]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:13][CH2:12][N:11]([CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:10][CH2:9][N:8]2[CH2:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:55]([CH:57]1[O:59][CH2:58]1)Cl>C1(C)C=CC=CC=1>[O:59]1[CH2:58][CH:57]1[CH2:55][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:18][N:17]([CH2:19][C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH2:16][CH2:15][N:14]([CH2:27][C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[CH2:13][CH2:12][N:11]([CH2:35][C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])[CH2:10][CH2:9][N:8]2[CH2:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[CH:51][CH:52]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 14346271HCID 14346271, compound

Product 1

HCID 21480268HCID 21480268, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

12.72 g (18.2 mmol) of 2-[4-hydroxybenzyl)-1,4,7,10-tetrakis-(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane (example 9d) is dissolved in 250 ml of toluene and mixed with 350 mg of sodium hydride (80% in paraffin, 18.3 mmol). It is warmed to 80° to 100° C. and mixed by instillation with a solution of 1.74 g (18.2 mmol) of epichlorohydrin in 50 ml of toluene. After refluxing for two hours, it is concentrated by evaporation and purified over a silica gel column. A colorless oil is obtained.

Workup

  1. temperatureIt is warmed to 80° to 100° C.
  2. temperatureAfter refluxing for two hours
  3. concentrationit is concentrated by evaporation
  4. custompurified over a silica gel column
  5. customA colorless oil is obtained

Sources & evidence

ORD record
ord-649913378aeb46a1b6bdb9a1014f5614
Source dataset
uspto-grants-1997_10
Patent number
US05681544

Reaction notes

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