Pentyl nitrite → Benzo[d]isothiazol-4-ol

HRID 1449122Notes

Reaction equation

HRID 1449122 reaction equation
N[C:2]1[C:10]2[S:9][N:8]=[CH:7][C:6]=2[C:5]([OH:11])=[CH:4][CH:3]=1.N(OCCCCC)=O>Cl.[Zn]>[OH:11][C:5]1[C:6]2[CH:7]=[N:8][S:9][C:10]=2[CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 10026Pentyl nitriteHCID 1356171871,2-Benzisothiazol-4-ol, 7-amino-

Product 1

HCID 135741992Benzo[d]isothiazol-4-ol

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
60 °C

Procedure

15.1 g of 7-amino-4-hydroxy-1,2-benzisothiazole are slowly suspended in 30 ml of concentrated hydrochloric acid and diazotized with 15 ml of amyl nitrite at from 0° to 5° C. After slowly heating the mixture to 60° C., 18 g of zinc dust are added in 10 portions and the mixture is refluxed until the evolution of gas has ceased. When the mixture has cooled, it is filtered through Celite and the filtrate is partitioned between dilute sodium hydroxide solution and chloroform. After acidifying the aqueous phase and repeatedly extracting it with methylene chloride, the combined organic extracts are dried over magnesium sulfate and freed from the solvent. This gives from 2 to 3 g of 4-hydroxy-1,2-benzisothiazole, which is identical with the compound prepared as described in Example 9.

Workup

  1. temperaturethe mixture is refluxed until the evolution of gas
  2. temperatureWhen the mixture has cooled
  3. filtrationit is filtered through Celite
  4. customthe filtrate is partitioned between dilute sodium hydroxide solution and chloroform
  5. extractionrepeatedly extracting it with methylene chloride
  6. dry with materialthe combined organic extracts are dried over magnesium sulfate

Sources & evidence

ORD record
ord-ed06b31a131d4fd2bec8df6cbe797862
Source dataset
uspto-grants-1980_02
Patent number
US04189433

Reaction notes

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