Methanol → 1-[2-Chloro-4-fluoro-5-(1,2,3,4,5,6-hexahydro-1,3-dioxo-isoindolyl)-phenylthio]-cyclopropanecarboxylic acid methyl ester

HRID 1646461Notes

Reaction equation

HRID 1646461 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:17](=[O:18])[CH:16]3[C:11](=[CH:12][CH2:13][CH2:14][CH2:15]3)[C:10]2=[O:19])=[CH:4][C:3]=1[S:20][C:21]1([C:24](Cl)=[O:25])[CH2:23][CH2:22]1.[CH3:27][OH:28].C(N(CC)CC)C>C(OC)(=O)C>[CH3:27][O:28][C:24]([C:21]1([S:20][C:3]2[CH:4]=[C:5]([N:9]3[C:17](=[O:18])[CH:16]4[C:11](=[CH:12][CH2:13][CH2:14][CH2:15]4)[C:10]3=[O:19])[C:6]([F:8])=[CH:7][C:2]=2[Cl:1])[CH2:23][CH2:22]1)=[O:25]

Participants

5

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 1317177131-[2-Chloro-4-fluoro-5-(1,2,3,4,5,6-hexahydro-1,3-dioxo-isoindolyl)-phenylthio]-cyclopropanecarboxylic acid chloride

Product 1

HCID 678545431-[2-Chloro-4-fluoro-5-(1,2,3,4,5,6-hexahydro-1,3-dioxo-isoindolyl)-phenylthio]-cyclopropanecarboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6584Methyl AcetateSolvent2×

Procedure

While stirring at room temperature, a solution of 1 g of 1-[2-chloro-4-fluoro-5-(1,2,3,4,5,6-hexahydro-1,3-dioxo-isoindolyl)-phenylthio]-cyclopropanecarboxylic acid chloride obtained in accordance with Example P9 in 10 ml of methyl acetate is added dropwise to a solution of 10 ml of methanol and 0.5 ml of triethylamine in 10 ml of methyl acetate. After stirring for 3 hours at room temperature, the resulting triethylamine hydrochloride is filtered off and the filtrate is concentrated by evaporation, yielding 0.9 g of 1-[2-chloro-4-fluoro-5-(1,2,3,4,5,6-hexahydro-1,3-dioxo-isoindolyl)-phenylthio]-cyclopropanecarboxylic acid methyl ester having a melting point of from +142° to +144° C.

Workup

  1. stirringAfter stirring for 3 hours at room temperature
  2. filtrationthe resulting triethylamine hydrochloride is filtered off
  3. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-a9f9ac6c4ac94a47b90a6b4f815024d8
Source dataset
uspto-grants-1993_01
Patent number
US05180418

Reaction notes

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