Diethyl Ether → 2-(1,3-thiazol-4-ylmethyl)-1H-isoindole-1,3(2H)-dione

HRID 1366671Notes

Reaction equation

CCOCC.Br[CH2:7][C:8](=O)[CH2:9][N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20].[CH:22]([NH2:24])=[S:23]>CCO>[S:23]1[CH:7]=[C:8]([CH2:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])[N:24]=[CH:22]1

Participants

Conditions

Temperature: 0 °C

Procedure

Ether (7.5 mL) was added to the above solution of 2-(3-bromo-2-oxopropyl)-1H-isoindole-1,3(2H)-dione and cooled to 0° C. in an ice/NaCl salt bath. Then thioformamide (European Journal of Medicinal Chemistry, 2004, 39, 867-872.) (1.20 g) in EtOH (8 mL) was added, and the reaction was stirred overnight. The solvents were evaporated and the reaction mixture was purified by RP-HPLC to provide 2-(1,3-thiazol-4-ylmethyl)-1H-isoindole-1,3(2H)-dione as a white solid. LCMS: (M+H)+=245.1.

Workup

customThe solvents were evaporated
customthe reaction mixture was purified by RP-HPLC

Sources & evidence

ORD record: ord-ec3aa91637114ab394cc9cb1d14fbe43
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893056B2

Reaction notes

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