Water → HCID 13577656, compound

HRID 2119140Notes

Reaction equation

HRID 2119140 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][C:5]([Cl:16])=[CH:4][C:3]=1[CH2:17][C:18]([OH:20])=[O:19].[Na].[CH2:22](I)[CH3:23].O>CC1OC(C)=C(C)C=1C>[CH2:22]([O:19][C:18](=[O:20])[CH2:17][C:3]1[CH:4]=[C:5]([Cl:16])[CH:6]=[C:7]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:2]=1[NH2:1])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 5360545SodiumHCID 12901227HCID 12901227, compound

Product 1

HCID 13577656HCID 13577656, compound

Reagents, catalysts & solvents 1

HCID 1391982,3,4,5-tetramethylfuranSolvent

Procedure

A solution of 3.12 g (0.1 mole) of 2-amino-3-benzoyl-5-chlorobenzeneacetic acid, sodium salt in 250 ml of dry tetramethylfuran was treated with 44 g of ethyl iodide (0.3 mole) under nitrogen and stirred for 2 hours. The resulting solution was then added to 1 liter of water and extracted several times with ethyl ether. The combined ether layers were washed with water, dried over sodium sulfate, filtered and stripped to yield a solid yellow residue. This material was recrystallized from absolute ethyl alcohol to give 1.5 g, yellow needles, m.p. 80°-82° C.

Workup

  1. extractionextracted several times with ethyl ether
  2. washThe combined ether layers were washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customto yield a solid yellow residue
  6. customThis material was recrystallized from absolute ethyl alcohol
  7. customto give 1.5 g, yellow needles, m.p. 80°-82° C.

Sources & evidence

ORD record
ord-55e446c4b89449d8837e5877d30fb622
Source dataset
uspto-grants-1987_07
Patent number
US04683242

Reaction notes

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