Acetic Acid → 5-Amino-3-(6-methoxy-m-tolyl)-1,2-benzisothiazole

HRID 1274544Notes

Reaction equation

HRID 1274544 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]2[C:14]3[CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=[CH:18][C:13]=3[S:12][N:11]=2)=[CH:5][CH:4]=1.C(O)(=O)C>[Fe].C(OCC)(=O)C>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]2[S:12][N:11]=[C:10]([C:6]3[CH:7]=[C:8]([CH3:9])[C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:14]=2[CH:15]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 698321503-(6-Methoxy-m-tolyl)-5-nitro-1,2-benzisothiazole

Product 1

HCID 698320455-Amino-3-(6-methoxy-m-tolyl)-1,2-benzisothiazoleYield 98.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3-(6-methoxy-m-tolyl)-5-nitro-1,2-benzisothiazole (63.0 g, 0.210 mol), 5% acetic acid (1.52 L, 1.21 mol) and ethyl acetate (975 mL) is heated to 65° C., treated portionwise with iron powder (58.6 g, 1.05 mol), stirred at 65° C., and filtered through quartz filter paper. The filtrate phases are separated and the aqueous phase is extracted with ethyl acetate. The organic phase and extracts are combined, washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain the title product as an orange oil (55.7 g, 98.1%) which is identified by NMR spectral analyses.

Workup

  1. filtrationfiltered through quartz
  2. filtrationfilter paper
  3. customThe filtrate phases are separated
  4. extractionthe aqueous phase is extracted with ethyl acetate
  5. washwashed sequentially with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d4afa29b70bd459ba4c92a1bcffa9286
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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