Potassium Iodide → HCID 131711329, compound

HRID 1704095Notes

Reaction equation

HRID 1704095 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[I-].[K+].Br[CH:16]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)=[CH:23][CH:22]=1)[C:17]([O:19][CH3:20])=[O:18]>O1CCCC1.CN(C)P(N(C)C)(N(C)C)=O>[CH3:20][O:19][C:17](=[O:18])[CH:16]([O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([N:2]([CH3:10])[CH3:1])[CH:4]=1)[C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][O:30][C:31]2[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=2)=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 74213-(Dimethylamino)phenolHCID 24758Sodium hydrideHCID 54245390HCID 54245390, compound

Product 1

HCID 131711329HCID 131711329, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

As described in Example 5, a mixture of 2.74 g of 3-dimethylaminophenol, 0.80 g of 60% sodium hydride-oil dispersion, 3.32 g of potassium iodide, one ml of hexamethylphosphoramide and 8.0 g of methyl bromo{p-[2-(p-chlorophenoxy)ethoxy]phenyl}acetate in 70 ml of tetrahydrofuran is refluxed for 18 hours and worked up to give 8.34 g of a gum. The gum is chromatographed on silica gel with dichloromethane as eluent to give 6.8 g of solid. Trituration with hexane-ether gives 3.50 g of crystals. Recrystallization gives crystals, mp 100°-101° C.

Workup

  1. temperatureis refluxed for 18 hours

Sources & evidence

ORD record
ord-05c5f98b85ce4339904c542816a29d47
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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