Acetic Acid → HCID 3002293, compound

HRID 1018786Notes

Reaction equation

HRID 1018786 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].C(O)(=O)C.[C:10]([NH:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[C:16]([F:22])[CH:15]=1)(=[O:12])[CH3:11]>O.C(O)C>[C:10]([NH:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[N:1][NH:2][C:3]([NH2:5])=[S:4])=[C:16]([F:22])[CH:15]=1)(=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2723789ThiosemicarbazideHCID 10214430HCID 10214430, compound

Product 1

HCID 3002293HCID 3002293, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 0.182 g (0.002 mole) of thiosemicarbazide (Aldrich T3,340-5) in 6 mL of water containing 0.4 mL of acetic acid was added to a solution of 0.36 g (0.002 mole) 4-acetamido-3-fluorobenzaldehyde (20) in 5 mL of ethanol at 70°. The mixture was stirred at this temperature for 30 minutes. A white precipitate developed in the reaction mixture, which was filtered after cooling down to give 0.22 g (44% crude) of white powder which was recrystallized from methanol and dried, yielding 0.12 g (24%) of 17 as white crystals, mp 232-235° (dec.). Infrared (IR) and NMR analysis gave the following results: IR (potassium bromide): 3441, 3317, 3167,1673 (C=O), 1600, 1534,1415 cm1. 1H nmr (90 MHz, DMSO-d6):δ 11.53 (1H, s, thiosemicarbazone NH), 10.35 (1H, s, amide NH), 8.25 (1H, s, imine H), 8.08 (1H; t, 3JH5-H6=9Hz, 4JF-H6=9 Hz; H-6), 8.04 (2H; br s; thiosemicarbazone NH2), 7.7 (1H; dd, 3JF-H3=12.6 Hz, 4JH5-H3=1.8 Hz; H-3), 7.27 (1H; dd, 3JH6-H5=9 Hz, 4JH3-H5=1.8 Hz; H-5), 2.11 (3H, s, CH3). Anal. Calcd. for C10H11FN40S (254.28): C, 47.23; H, 4.36; F, 7.47; N, 22.03; S, 12.61. Found: C, 46.88; H, 4.35; F, 7.30; N, 21.62; S, 12.11.

Workup

  1. filtrationwas filtered
  2. temperatureafter cooling down
  3. customto give 0.22 g (44% crude) of white powder which
  4. customwas recrystallized from methanol
  5. customdried

Sources & evidence

ORD record
ord-dd1b1c24eb554c4ba9d70e82d2acb43c
Source dataset
uspto-grants-2002_11
Patent number
US06482982B1

Reaction notes

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