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

HRID 369589Notes

Reaction equation

HRID 369589 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-9071b6e3a0044165873c88d80deb5c0f
Source dataset
uspto-grants-2000_10
Patent number
US06140270

Reaction notes

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