(Methylthio)acetic acid → N-[2-chloro-4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]phenyl]methyl-2-(methylthio) acetamide

HRID 1880237Notes

Reaction equation

HRID 1880237 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:13][C:12]([C:18]3[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[C:20]([Cl:26])[CH:19]=3)([C:14]([F:17])([F:16])[F:15])[O:11][N:10]=2)=[CH:5][C:4]=1[Cl:27].[CH3:28][S:29][CH2:30][C:31](O)=[O:32].Cl.CN(C)CCCN=C=NCC.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:27][C:4]1[CH:5]=[C:6]([C:9]2[CH2:13][C:12]([C:18]3[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[C:20]([Cl:26])[CH:19]=3)([C:14]([F:17])([F:16])[F:15])[O:11][N:10]=2)[CH:7]=[CH:8][C:3]=1[CH2:2][NH:1][C:31](=[O:32])[CH2:30][S:29][CH3:28]

Participants

7

Reactant 4

HCID 75551(Methylthio)acetic acidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 446282993-(4-Aminomethyl-3-chlorophenyl)-5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

Product 1

HCID 49763421N-[2-chloro-4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]phenyl]methyl-2-(methylthio) acetamide

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 0.11 g of 3-(4-aminomethyl-3-chlorophenyl)-5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole, 0.051 g of (methylthio) acetic acid and 0.048 g of triethylamine in 2 mL of chloroform, 0.092 g of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride was added and the resultant mixture was stirred at room temperature for 15 hours. After the completion of the reaction, 2 mL of a saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture and the organic phase was separated off, followed by purifying the organic phase as it was by preparative medium pressure liquid chromatography eluting with ethyl acetate-hexane (a gradient from 1:4 to 1:1) using a medium pressure preparative apparatus (trade name: YFLC-Wprep; manufactured by Yamazen Corporation) to obtain 0.12 g of the objective substance as a colorless resinoid.

Workup

  1. additionwas added to the reaction mixture
  2. customthe organic phase was separated off
  3. customby purifying the organic phase as it
  4. washeluting with ethyl acetate-hexane (a gradient from 1:4 to 1:1)
  5. customto obtain 0.12 g of the objective substance as a colorless resinoid

Sources & evidence

ORD record
ord-94d6b82d4c6747d9aab98e30b239e20e
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

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