Water → HCID 14835399, compound

HRID 1199022Notes

Reaction equation

HRID 1199022 reaction equation
[C:1]1([C:7]2[O:8][N:9]=[C:10]3[C:15]([CH2:16][C:17]([OH:19])=[O:18])=[CH:14][CH:13]=[CH:12][C:11]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20](I)[CH3:21].O>CN(C)C=O>[CH2:20]([O:18][C:17](=[O:19])[CH2:16][C:15]1[C:10]2[C:11](=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:8][N:9]=2)[CH:12]=[CH:13][CH:14]=1)[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 6340IodoethaneHCID 15634759HCID 15634759, compound

Product 1

HCID 14835399HCID 14835399, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred slurry of 0.7 g (0.014 mole) of washed (petroleum ether), 50% sodium hydride/oil in 5 ml of dry dimethylformamide was added a solution of 2.9 g (0.012 mole) of 3-phenyl-2,1-benzisoxazol-7-acetic acid in 15 ml of dimethylformamide. The mixture was stirred at ambient temperature for 10 minutes and then 2.0 g (0.013 mole) of ethyl iodide was added. The dark solution was stirred at ambient temperature for 1 hr and then poured into 500 ml of water and let stand overnight. The mixture was filtered and the collected solid was recrystallized from 2-propanol to give 0.2 g (6%) of solid, m.p. 97°-98° C.

Workup

  1. washTo a stirred slurry of 0.7 g (0.014 mole) of washed (petroleum ether), 50% sodium hydride/oil in 5 ml of dry dimethylformamide
  2. stirringThe dark solution was stirred at ambient temperature for 1 hr
  3. waitlet stand overnight
  4. filtrationThe mixture was filtered
  5. customthe collected solid was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-788f26a375df41f29f66ba457ee3b91c
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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