Ethylthioacetic acid → HCID 49763423, compound

HRID 1880244Notes

Reaction equation

HRID 1880244 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[CH2:15][C:14]([C:20]3[CH:25]=[C:24]([Cl:26])[C:23]([Cl:27])=[C:22]([Cl:28])[CH:21]=3)([C:16]([F:19])([F:18])[F:17])[O:13][N:12]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][NH:9][CH3:10].[CH2:29]([S:31][CH2:32][C:33]([OH:35])=O)[CH3:30].Cl.CN(C)CCCN=C=NCC>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[CH2:15][C:14]([C:20]3[CH:25]=[C:24]([Cl:26])[C:23]([Cl:27])=[C:22]([Cl:28])[CH:21]=3)([C:16]([F:19])([F:17])[F:18])[O:13][N:12]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][N:9]([CH3:10])[C:33](=[O:35])[CH2:32][S:31][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 69387Ethylthioacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86649763HCID 86649763, compound

Product 1

HCID 49763423HCID 49763423, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.10 g of 3-[3-chloro-4-[N-(methyl)aminomethyl]phenyl]-5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole and 0.038 g of (ethylthio)acetic acid in 3 mL of dichloromethane, 0.089 g of 1-[3-(dimethylamino) propyl]-3-ethylcarbodiimide hydrochloride was added and the resultant mixture was stirred at room temperature for 3 hours. After the completion of the reaction, the reaction mixture was washed with water (5 mL×1) and then dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure. The resultant residue was purified by preparative medium pressure liquid chromatography eluting with ethyl acetate-hexane (a gradient from 1:5 to 1:3) using a medium pressure preparative apparatus (trade name: YFLC-Wprep; manufactured by Yamazen Corporation) to obtain 0.083 g of the objective substance as a colorless resinoid.

Workup

  1. customAfter the completion of the reaction
  2. washthe reaction mixture was washed with water (5 mL×1)
  3. dry with materialdried over saturated saline and anhydrous sodium sulfate in this order
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resultant residue was purified by preparative medium pressure liquid chromatography
  6. washeluting with ethyl acetate-hexane (a gradient from 1:5 to 1:3)
  7. customto obtain 0.083 g of the objective substance as a colorless resinoid

Sources & evidence

ORD record
ord-020e4ff0f45d40278c9e75b550066678
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

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