Acetic Acid → N-acetyl-N-(5-amino-benzo[d]isothiazol-3-yl)-acetamide

HRID 1766301Notes

Reaction equation

HRID 1766301 reaction equation
[C:1]([N:4]([C:8]1[C:12]2[CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=[CH:16][C:11]=2[S:10][N:9]=1)[C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].C(O)(=O)C.C(=O)(O)[O-].[Na+]>[Fe].C(OCC)(=O)C>[C:1]([N:4]([C:8]1[C:12]2[CH:13]=[C:14]([NH2:17])[CH:15]=[CH:16][C:11]=2[S:10][N:9]=1)[C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 21110339N-acetyl-N-(5-nitro-benzo[d]isothiazol-3-yl)-acetamide

Product 1

HCID 21110338N-acetyl-N-(5-amino-benzo[d]isothiazol-3-yl)-acetamideYield 38%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of N-acetyl-N-(5-nitro-benzo[d]isothiazol-3-yl)-acetamide (1.133 g, 4.06 mmol) in a 1:1 acetic acid:ethyl acetate solution (70 mL) at 50° C. was added iron powder (680 mg, 12.2 mmol). The resulting mixture was stirred at 50° C. for 5 h, then cooled, poured into saturated sodium bicarbonate and extracted into ethyl acetate. The organic layers were combined, washed with water and then brine, dried (MgSO4), filtered, and evaporated. The residue was purified using flash chromatography on silica to afford the desired amine as an orange solid (383 mg, 38%), single spot at Rf 0.30 (1:1 dichloromethane:ethyl acetate). mp 213.0-214.2° C. 1H NMR (CDCl3): δ 8.56 (1H, d, J=9.2 Hz), 7.48 (d, J=2.7 Hz), 7.14 (1H, dd, J=9.2, 2.7 Hz), 2.62 (3H, s), 2.56 (3H, s).

Workup

  1. temperaturecooled
  2. extractionextracted into ethyl acetate
  3. washwashed with water
  4. dry with materialbrine, dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-32b750b3c32c410ab54be4422cf1fee4
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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