Acetic Acid → 7-Amino-4-benzyloxy-1,2-benzisothiazole

HRID 1449120Notes

Reaction equation

HRID 1449120 reaction equation
[N+:1]([C:4]1[C:12]2[S:11][N:10]=[CH:9][C:8]=2[C:7]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1)([O-])=O.O.C(O)(=O)C.N>[Fe].C(O)CC>[NH2:1][C:4]1[C:12]2[S:11][N:10]=[CH:9][C:8]=2[C:7]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 962WaterHCID 203499427-Nitro-4-benzyloxy-1,2-benzisothiazole

Product 1

HCID 203499357-Amino-4-benzyloxy-1,2-benzisothiazoleYield 100%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 10311-PropanolSolvent

Procedure

28.6 g of 7-nitro-4-benzyloxy-1,2-benzisothiazole are added in portions to a boiling mixture of 67 ml of water, 30 g of iron powder, 3 ml of glacial acetic acid and 167 ml of n-propanol and the mixture is then refluxed for a further hour. When it has cooled, it is neutralized with concentrated ammonia solution and filtered. The filter residue is washed with methylene chloride and the combined wash solutions are dried over magnesium sulfate and freed from the solvent under reduced pressure. 25.1 g (100% of theory) of 7-amino-4-benzyloxy-1,2-benzisothiazole of melting point 126°-128° C. are obtained.

Workup

  1. temperaturethe mixture is then refluxed for a further hour
  2. temperatureWhen it has cooled
  3. filtrationfiltered
  4. washThe filter residue is washed with methylene chloride
  5. dry with materialthe combined wash solutions are dried over magnesium sulfate

Sources & evidence

ORD record
ord-d0ff86413b954b0d97b5004a7967a224
Source dataset
uspto-grants-1980_02
Patent number
US04189433

Reaction notes

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