Water → 223508-81-4

HRID 611626Notes

Reaction equation

HRID 611626 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:28]=[CH:27][C:6]([CH2:7][NH:8][C:9](=[O:26])[C:10]2[CH:15]=[C:14]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])[CH:13]=[CH:12][C:11]=2[O:24]C)=[CH:5][CH:4]=1.B(Br)(Br)Br.C(Cl)Cl.C(=O)=O.CC(C)=O.O>C(Cl)Cl>[F:30][C:2]([F:1])([F:29])[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9](=[O:26])[C:10]2[CH:15]=[C:14]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])[CH:13]=[CH:12][C:11]=2[OH:24])=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1511835-[(2,4-Dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxy-N-{[4-(trifluoromethyl)phenyl]methyl}benzamideHCID 18522661Acetone cardiceHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 15871344223508-81-4Yield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-(4-trifluoromethylbenzyl)-5-(2,4-dioxothiazolidin-5-yl)methyl-2-methoxybenzamide (800 mg) in anhydrous methylene chloride (30 ml), a 1.0N boron tribromide-methylene chloride solution (2.20 ml) was slowly added dropwise in an argon atmosphere under cooling with dry ice-acetone and stirring. After stirred for 6 hours at room temperature, the reaction liquor was allowed to stand for 3 days. After water was added and the mixture was stirred for 30 minutes, this was concentrated under reduced pressure. Ethyl acetate was added to the residue, which was washed with water and then dried over anhydrous sodium sulfate. This was concentrated under reduced pressure and the residue was purified by means of silica gel column chromatography (developing solvent; methylene chloride:methanol=40:1) to obtain 618 mg (80%) of aimed compound as crystals. These were recrystallized from ethanol-water to obtain purified aimed compound as a light brown powdery crystals. Melting point 146.0~148.0° C.

Workup

  1. stirringAfter stirred for 6 hours at room temperature
  2. stirringthe mixture was stirred for 30 minutes
  3. concentrationthis was concentrated under reduced pressure
  4. additionEthyl acetate was added to the residue, which
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThis was concentrated under reduced pressure
  8. customthe residue was purified by means of silica gel column chromatography (developing solvent; methylene chloride:methanol=40:1)

Sources & evidence

ORD record
ord-a34e4e0ba232404dbc6a3be79a1e80ac
Source dataset
uspto-grants-1999_12
Patent number
US06001862

Reaction notes

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