Water → HCID 57845841, compound

HRID 735112Notes

Reaction equation

HRID 735112 reaction equation
C(=O)([O-])O.[Na+].O.O.[Sn](Cl)Cl.[N+:11]([C:14]1[CH:15]=[C:16]([NH:28][C:29](=[O:43])[C:30]#[C:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][C:33]=2[Cl:42])[CH:17]=[CH:18][C:19]=1[O:20][CH2:21][CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])([O-])=O.O>C(OCC)(=O)C>[NH2:11][C:14]1[CH:15]=[C:16]([NH:28][C:29](=[O:43])[C:30]#[C:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:39])([F:40])[F:41])=[CH:34][C:33]=2[Cl:42])[CH:17]=[CH:18][C:19]=1[O:20][CH2:21][CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 57845856HCID 57845856, compound

Product 1

HCID 57845841HCID 57845841, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

870 mg (10.3 mmol) of sodium hydrogen carbonate and 1.17 g (5.17 mmol) of tin (II) chloride dihydrate are added at ambient temperature to a solution of 250 mg (0.52 mmol) of 3-(2-chloro-4-trifluoromethylphenyl)propynoic acid-[3-nitro-4-(2-diethylaminoethoxy)phenyl]amide in 50 mL of ethyl acetate. The mixture is refluxed for 12 hours. After cooling, water is added and the organic phase is separated off. The aqueous phase is extracted twice more with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is eliminated. The purification of the residue is carried out by column chromatography on Alox (eluant: dichloromethane/methanol (39:1)). Yield: 100 mg (43% of theory); melting point: 127° C.-130° C.; C22H23ClF3N3O2 (M=453.89); calc.: molecular ion peak (M+H)+: 454/456; found: molecular ion peak (M+H)+: 454/456; Rf value: 0.60 (Alox, dichloromethane/methanol (39:1)).

Workup

  1. temperatureThe mixture is refluxed for 12 hours
  2. temperatureAfter cooling
  3. customthe organic phase is separated off
  4. extractionThe aqueous phase is extracted twice more with ethyl acetate
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. customThe purification of the residue

Sources & evidence

ORD record
ord-c4ad55d59e09483da90a8b0dad0f5e4c
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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