Iodoethane → HCID 13577658, compound

HRID 1589208Notes

Reaction equation

HRID 1589208 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:17][C:18]([OH:20])=[O:19].[Na].[CH2:22](I)[CH3:23]>CN(C)C=O>[CH2:22]([O:19][C:18](=[O:20])[CH2:17][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=2)[C:2]=1[NH2:1])[CH3:23]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 60726BromfenacHCID 5360545Sodium

Product 1

HCID 13577658HCID 13577658, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A slurry of 35.6 g (0.1 mole) of 2-amino-3-(4-bromobenzoyl)benzeneacetic acid, sodium salt in 500 ml of dimethylformamide was treated with 32.0 g (0.2 mole) of ethyl iodide and stirred at ambient temperature for 24 hr. The mixture was filtered and the filtrate was poured into 3.5 liters of water. The solid which precipitated was collected by filtration, washed with water and recrystallized from absolute ethanol to yield 26.8 g (74%) of the titled compound as tiny gold needles, m.p. 107°-109° C.

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was poured into 3.5 liters of water
  3. customThe solid which precipitated
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customrecrystallized from absolute ethanol

Sources & evidence

ORD record
ord-6452e0f68af545bc8182abef495f6713
Source dataset
uspto-grants-1986_02
Patent number
US04568695

Reaction notes

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