4-(Trifluoromethyl)dihydro-2H-pyran-2,6(3H)-dione → N-[4-chloro-2-fluoro-5-(1-methoxycarbonyl-cyclobutylthio)-phenyl]-3-trifluoromethylglutaric acid monoamide

HRID 1646462Notes

Reaction equation

HRID 1646462 reaction equation
[F:1][C:2]([F:12])([F:11])[CH:3]1[CH2:9][C:8](=[O:10])[O:7][C:5](=[O:6])[CH2:4]1.[CH3:13][O:14][C:15]([C:17]1([S:21][C:22]2[CH:27]=[C:26]([NH2:28])[C:25]([F:29])=[CH:24][C:23]=2[Cl:30])[CH2:20][CH2:19][CH2:18]1)=[O:16]>C1C=CC=CC=1>[Cl:30][C:23]1[C:22]([S:21][C:17]2([C:15]([O:14][CH3:13])=[O:16])[CH2:18][CH2:19][CH2:20]2)=[CH:27][C:26]([NH:28][C:8](=[O:10])[CH2:9][CH:3]([C:2]([F:1])([F:12])[F:11])[CH2:4][C:5]([OH:7])=[O:6])=[C:25]([F:29])[CH:24]=1

Participants

4

Reactant 2

HCID 157442444-(Trifluoromethyl)dihydro-2H-pyran-2,6(3H)-dioneHCID 544812611-(5-Amino-2-chloro-4-fluorophenylthio)-cyclobutanecarboxylic acid methyl ester

Product 1

HCID 21749659N-[4-chloro-2-fluoro-5-(1-methoxycarbonyl-cyclobutylthio)-phenyl]-3-trifluoromethylglutaric acid monoamideYield 84.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3.6 g of 3-trifluoromethylglutaric anhydride and 5.8 g of 1-(5-amino-2-chloro-4-fluoro-phenylthio)-cyclobutanecarboxylic acid methyl ester in 65 ml of benzene is heated under reflux for 3 hours while stirring. The resulting precipitate is then separated off, washed with diisopropyl ether and dried, yielding 7.9 g of N-[4-chloro-2-fluoro-5-(1-methoxycarbonyl-cyclobutylthio)-phenyl]-3-trifluoromethylglutaric acid monoamide having a melting point of from +165° to +167° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. customThe resulting precipitate is then separated off
  4. washwashed with diisopropyl ether
  5. customdried

Sources & evidence

ORD record
ord-15a560a22a2049c48e87c303fa561198
Source dataset
uspto-grants-1993_01
Patent number
US05180418

Reaction notes

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