Water → 2-(2,3-Dichloro-phenyl)-thiazole-4-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester

HRID 1990992Notes

Reaction equation

HRID 1990992 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=[O:15])[N:13]=1.C(N([CH:23]([CH3:25])C)CC)(C)C.C([NH3+])C.[OH2:29].C[N:31]([CH:33]=[O:34])[CH3:32]>O1CCOCC1>[O:29]=[C:32]1[CH2:25][CH2:23][C:33](=[O:34])[N:31]1[O:15][C:14]([C:12]1[N:13]=[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])[S:10][CH:11]=1)=[O:16]

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27439872-(2,3-dichlorophenyl)-1,3-thiazole-4-carboxylic AcidHCID 3427831Ethanaminium

Product 1

HCID 589249272-(2,3-Dichloro-phenyl)-thiazole-4-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl esterYield 87%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-(2,3-Dichloro-phenyl)-thiazole-4-carboxylic acid (4.1 g, 15 mmol) was dissolved in a mixture of 50 mL of DMF and 50 mL of dioxane. To this solution diisopropylethylamine (7.8 mL, 45 mmol) and ethanaminium, N-[(dimethylamino)[(2,5-dioxo-1-pyrrolidinyl)oxy]methylene]-N-methyl-, tetrafluoroborate(1-) (TSTU, Aldrich Inc.; 6.8 g, 22.5 mmol) was added. The reaction mixture was stirred at room temperature for 3 h after which 150 mL water was added and the organic layer was separated. The organic layer was extracted with 50 mL water twice, dried and concentrated. The crude mixture was washed with 100 mL isopropanol, to give 2-(2,3-dichloro-phenyl)-thiazole-4-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester (4.8 g, 87% yield) and used without further purification.

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. extractionThe organic layer was extracted with 50 mL water twice
  4. customdried
  5. concentrationconcentrated
  6. washThe crude mixture was washed with 100 mL isopropanol

Sources & evidence

ORD record
ord-5b1a48f56d684c1f969be01d81dd89c9
Source dataset
uspto-grants-2010_01
Patent number
US07645773B2

Reaction notes

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