Methyl Ethyl Ketone → HCID 70051691, compound

HRID 266462Notes

Reaction equation

HRID 266462 reaction equation
[CH2:1]([N:8]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([OH:20])=[CH:15][CH:16]=2)[S:9]1(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27]Br.C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>CN(C)C=O>[CH2:1]([N:8]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([O:20][CH2:27][CH2:26][O:25][CH2:24][CH2:23][O:22][CH3:21])=[CH:15][CH:16]=2)[S:9]1(=[O:11])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 1235321-Bromo-3,6-dioxaheptaneHCID 70053010HCID 70053010, compound

Product 1

HCID 70051691HCID 70051691, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-benzyl-6-hydroxysaccharin (0.86 g), 2-bromoethyl 2-methoxyethyl ether (d=1.347, 0.45 mL), potassium carbonate (1.24 g), methyl ethyl ketone (50 mL) and dimethylformamide (2 mL) was heated under reflux for five hours, then poured into ice-water (500 mL). The resulting solid was collected, washed with water and dried affording 2-benzyl-6-[2-(2-methoxyethoxy)ethoxy]saccharin (0.92 g, 78% yield, mp 86°-88° C.).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for five hours
  3. customThe resulting solid was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-733dbf6e7af74257b4b4a47719fb9b29
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

Loading…