Water → HCID 178505614, compound

HRID 568694Notes

Reaction equation

HRID 568694 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Al+3].[Cl-].[Cl-].[Cl-].[Cl:9][C:10]1[C:18]2[O:17][N:16]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[C:14]=2[CH:13]=[CH:12][C:11]=1[O:26][CH2:27][C:28]#[N:29].O>C1COCC1>[Cl:9][C:10]1[C:18]2[O:17][N:16]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[C:14]=2[CH:13]=[CH:12][C:11]=1[O:26][CH2:27][C:28]1[NH:29][N:3]=[N:2][N:1]=1

Participants

6

Reactant 4

HCID 962WaterHCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 14012513HCID 14012513, compound

Product 1

HCID 178505614HCID 178505614, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.35 g NaN3 and 2.25 g of AlCl3 are stirred in 50 ml THF at reflux for 0.5 hour. A solution of 5 g {[7-chloro-3-(2-fluorophenyl)-1,2-benzisoxazole-6-yl]oxy}acetonitrile, of Example 50, in 50 ml THF is added and the reaction mixture is stirred at reflux for about 120 hours. To the reaction mixture is added water and the solvent is removed. The residue is treated with dilute HCl and extracted with CHCl3. Upon attempted extraction of the chloroform solution with 15% NaOH a precipitate forms which is filtered, dissolved in hot water and acidified to afford 7-chloro-3-(2-fluorophenyl)-6-{[5-tetrazolylmethyl]oxy}-1,2-benzisoxazole, mp 198°-200° C.

Workup

  1. temperatureat reflux for 0.5 hour
  2. temperatureat reflux for about 120 hours
  3. customthe solvent is removed
  4. additionThe residue is treated with dilute HCl
  5. extractionextracted with CHCl3
  6. extractionextraction of the chloroform solution with 15% NaOH a precipitate forms which
  7. filtrationis filtered
  8. dissolutiondissolved in hot water

Sources & evidence

ORD record
ord-11cd8fa99eda4004b171202f38260145
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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