Iodoethane → HCID 13960919, compound

HRID 2119142Notes

Reaction equation

HRID 2119142 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][C:5]([Cl:17])=[CH:4][C:3]=1[CH2:18][C:19]([OH:21])=[O:20].[Na].[CH2:23](I)[CH3:24]>CN(C)C=O.O>[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][C:5]([Cl:17])=[CH:4][C:3]=1[CH2:18][C:19]([O:21][CH2:23][CH3:24])=[O:20]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 5360545SodiumHCID 13408276HCID 13408276, compound

Product 1

HCID 13960919HCID 13960919, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 40.9 g (0.1 mole) of 2-amino-3-(4-bromobenzoyl)-5-chlorobenzeneacetic acid, sodium salt, monohydrate in 400 ml of dimethylformamide was treated with 32.0 g (0.2 mole) of ethyl iodide and the solution was let stand at ambient temperature overnight. The solution was poured in 3.5 liters of cold water and a solid gradually crystallized. The solid was collected by filtration, washed with water, and recrystallized from absolute ethanol to yield 36.2 g (91%) of title compound, a yellow solid, m.p. 92°-94° C.

Workup

  1. customat ambient temperature
  2. customovernight
  3. customa solid gradually crystallized
  4. filtrationThe solid was collected by filtration
  5. washwashed with water
  6. customrecrystallized from absolute ethanol

Sources & evidence

ORD record
ord-89478fbb854340a290790d94f18f3550
Source dataset
uspto-grants-1987_07
Patent number
US04683242

Reaction notes

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