Thiazolidine → HCID 68108646, compound

HRID 385128Notes

Reaction equation

HRID 385128 reaction equation
[O:1]=[S:2]1(=[O:28])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([C:11]([C:13]2[CH:14]=[C:15]([C:24]([F:27])([F:26])[F:25])[C:16]([O:22][CH3:23])=[C:17]([CH:21]=2)[C:18](O)=[O:19])=[O:12])[CH2:3]1.[S:29]1[CH2:33][CH2:32][NH:31][CH2:30]1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH3:23][O:22][C:16]1[C:15]([C:24]([F:27])([F:26])[F:25])=[CH:14][C:13]([C:11]([N:4]2[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[S:2](=[O:28])(=[O:1])[CH2:3]2)=[O:12])=[CH:21][C:17]=1[C:18]([N:31]1[CH2:32][CH2:33][S:29][CH2:30]1)=[O:19]

Participants

5

Reactant 3

HCID 10444ThiazolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68108180HCID 68108180, compound

Product 1

HCID 68108646HCID 68108646, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(1,1-dioxo-2,3-dihydro-1,3-benzothiazole-3-carbonyl)-2-methoxy-3-trifluoromethylbenzoic acid (277 mg) was dissolved in dichloromethane (3 mL), thiazolidine (0.10 mL) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (238 mg) were added to the solution, and then the mixture was stirred at room temperature for 19 hours. The solvent was distilled off under reduced pressure and 1N hydrochloric acid was added and then the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, 1N sodium hydroxide and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (138 mg) as a colorless oily substance.

Workup

  1. distillationThe solvent was distilled off under reduced pressure and 1N hydrochloric acid
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with 1N hydrochloric acid, 1N sodium hydroxide and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-ba8599c8d94144c0b5b355801e683d67
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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