Iodine → N-(5-Furan-3-yl-4-phenyl-thiazol-2-yl)-formamide

HRID 604479Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)=[CH:2]1.[NH2:15][C:16]([NH2:18])=[S:17].II.[NH4+].[OH-].CN([CH:26]=[O:27])C>O>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[S:17][C:16]([NH:18][CH:26]=[O:27])=[N:15][C:7]=2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:2]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-furan-3-yl-1-phenyl-ethanone (5.7 g, 31 mmol) and thiourea (4.7 g, 61 mmol) in DMF (57 mL) was and added iodine (7.8 g, 31 mmol). The reaction mixture was heated at 100° C. overnight, then it was diluted with water and made alkaline with saturated aqueous NH4OH, and extracted with ether. The organic phases were washed with water, dried over sodium sulfate, concentrated and purified on neutral Al2O3 using 50% ethyl acetate in hexane as eluent. Yield: 5.7 g, 69%.

Workup

extractionextracted with ether
washThe organic phases were washed with water
dry with materialdried over sodium sulfate
concentrationconcentrated
custompurified on neutral Al2O3 using 50% ethyl acetate in hexane as eluent

Sources & evidence

ORD record: ord-d0bd42ae18bd45618907eeee605def21
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910613B2

Reaction notes

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