Hydrazine, ethyl-, ethanedioate (1:1) → HCID 22065117, compound

HRID 1835394Notes

Reaction equation

HRID 1835394 reaction equation
CS[C:3]([C:25]1[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=1[F:32])=[N:4][C:5]([C:7]1[S:8][C:9]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=2)=[C:10]([Br:13])[C:11]=1[CH3:12])=O.C(O)(=O)C(O)=O.[CH2:39]([NH:41][NH2:42])[CH3:40]>C1(C)C=CC=CC=1.CCOCC>[Cl:31][C:30]1[CH:29]=[CH:28][CH:27]=[C:26]([F:32])[C:25]=1[C:3]1[N:4]=[C:5]([C:7]2[S:8][C:9]([C:14]3[CH:15]=[CH:16][C:17]([O:20][C:21]([F:23])([F:24])[F:22])=[CH:18][CH:19]=3)=[C:10]([Br:13])[C:11]=2[CH3:12])[N:41]([CH2:39][CH3:40])[N:42]=1

Participants

5

Reactant 2

HCID 96181Hydrazine, ethyl-, ethanedioate (1:1)HCID 22065140HCID 22065140, compound

Product 1

HCID 22065117HCID 22065117, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

Methyl-N-{[3-methyl-4-bromo-5-(4-trifluoromethoxyphenyl)-2-thienyl]-carbonyl}-2-fluoro-6-chlorobenzenecarbimidothioate (0.85 g, 1.5 mmol) and ethylhydrazine oxalate (0.90 g, 6 mmol) were combined in toluene (5 mL) and stirred 64 h at 25° C. and heated to reflux for 18 h. The reaction mixture was diluted with ether and washed with 0.1 M hydrochloric acid and brine, dried over anhydrous magnesium sulfate and concentrated to a crude pale yellow oil. Chromatography (silica gel, 10% ethylacetate/hexane) afforded the product as a clear oil (0.250 mg, 30%): 1H NMR (CDCl3) δ 7.73 (2H, d), 7.0-7.5 (5H, m), 4.3 (2H, q), 2.40 (3H, s), 1.55 (3H, t); EI/MS 546 m/e (M+).

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 h
  3. washwashed with 0.1 M hydrochloric acid and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to a crude pale yellow oil

Sources & evidence

ORD record
ord-7cf63fdd0aa64e65b7450552ebd43e16
Source dataset
uspto-grants-2004_08
Patent number
US06770665B2

Reaction notes

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