Acetic Acid → 5-Amino-2-(isopropylthio)-N-methylbenzamide

HRID 735525Notes

Reaction equation

HRID 735525 reaction equation
[CH:1]([S:4][C:5]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:6]=1[C:7]([NH:9][CH3:10])=[O:8])([CH3:3])[CH3:2].O.C(O)(=O)C>C(O)C.[Fe]>[NH2:15][C:12]1[CH:13]=[CH:14][C:5]([S:4][CH:1]([CH3:3])[CH3:2])=[C:6]([CH:11]=1)[C:7]([NH:9][CH3:10])=[O:8]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 57842864HCID 57842864, compound

Product 1

HCID 578428575-Amino-2-(isopropylthio)-N-methylbenzamideYield 93%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
115 °C

Procedure

A suspension of 16B (1.2 g, 4.7 mmol) in a mixture of ethanol (30 mL), water (5 mL), and acetic acid (3.3 mL, 5.8 mmol) was heated by a 115° C. oil bath. Iron powder (1.80 g, 32.2 mmol) was added portionwise over 1 h. The reaction mixture was cooled to rt, filtered, and washed with ethyl acetate. Sodium bicarbonate solution was added until it was basic. The reaction mixture was extracted with ethyl acetate (3×) and the combined organics were washed with saturated sodium bicarbonate and brine, dried (MgSO4), and concentrated in vacuo to give 16C (0.98 g, 93%) as a beige solid. MS (ESI) m/z 225.1 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationfiltered
  3. washwashed with ethyl acetate
  4. additionSodium bicarbonate solution was added until it
  5. extractionThe reaction mixture was extracted with ethyl acetate (3×)
  6. washthe combined organics were washed with saturated sodium bicarbonate and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e5653d5bfca45eda1892cb75d8caa04
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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