Acetic Acid → HCID 19047040, compound

HRID 1780593Notes

Reaction equation

HRID 1780593 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-])=O)=[C:6]([C:8]2[S:9][CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:12]=2)[CH:7]=1.C(O)(=O)C>[Fe].O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:17])=[C:6]([C:8]2[S:9][CH:10]=[C:11]([C:13]([F:15])([F:14])[F:16])[N:12]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 19047035HCID 19047035, compound

Product 1

HCID 19047040HCID 19047040, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

The product from Step D (3.1 g, 0.011 mol) was suspended in a mixture of glacial acetic acid (15 mL) and water (5 mL). The mixture was heated on a steam bath to a temperature of 65° C. Iron powder (1.9 g, 0.035 mol) was then added in small portions (exothermic). Care was taken during the addition to ensure that the temperature did not exceed 75° C. Once the iron had been added, heating at 75° C. was continued for another 10 min. The reaction mixture was hot-filtered onto 30 g cracked ice. After the ice melted, the aqueous mixture was extracted with dichloromethane (3×20 mL). The combined extracts were washed with saturated sodium bicarbonate and brine (30 mL each). The dried (MgSO4) solution was concentrated to furnish 1.4 g (53% yield) of the title compound as a white solid melting at 100°-103° C. 1H NMR (400 MHz, CDCl3) δ 7.62 (s,1H), 7.39 (s,1H), 7.03-7.05 (m,1H), 6.69-6.71 (m,1H), 5.82 (br s,2H), 2.28 (s,3H).

Workup

  1. additionCare was taken during the addition
  2. customdid not exceed 75° C
  3. temperatureheating at 75° C.
  4. filtrationThe reaction mixture was hot-filtered onto 30 g
  5. extractionthe aqueous mixture was extracted with dichloromethane (3×20 mL)
  6. washThe combined extracts were washed with saturated sodium bicarbonate and brine (30 mL each)
  7. dry with materialThe dried (MgSO4) solution
  8. concentrationwas concentrated

Sources & evidence

ORD record
ord-6f5eb290ada644699e1b9529d5c4d6a3
Source dataset
uspto-grants-1997_05
Patent number
US05631206

Reaction notes

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