2-Bromo-1-(2,5-dimethylfuran-3-yl)ethan-1-one → Ethyl 3-[4-(2,5-dimethyl-3-furyl)-2-thiazolyl]benzoate

HRID 1264948Notes

Reaction equation

HRID 1264948 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[S:3])[NH2:2].Br[CH2:16][C:17]([C:19]1[CH:23]=[C:22]([CH3:24])[O:21][C:20]=1[CH3:25])=O>>[CH3:25][C:20]1[O:21][C:22]([CH3:24])=[CH:23][C:19]=1[C:17]1[N:2]=[C:1]([C:4]2[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[S:3][CH:16]=1

Participants

3

Reactant 2

HCID 186138692-Bromo-1-(2,5-dimethylfuran-3-yl)ethan-1-oneHCID 18613909Ethyl 3-thiocarbamoylbenzoate

Product 1

HCID 18613843Ethyl 3-[4-(2,5-dimethyl-3-furyl)-2-thiazolyl]benzoateYield 16%

Procedure

In the same manner as in Example 28, ethyl 3-thiocarbamoylbenzoate was reacted with 3-bromoacetyl-2,5-dimethylfuran to obtain ethyl 3-[4-(2,5-dimethyl-3-furyl)-2-thiazolyl]benzoate. The product was recrystallized from ethanol. Yield: 16%, Pale yellow prisms. Melting point: 100 to 101° C.

Sources & evidence

ORD record
ord-ca2c2e0b69764cf1a893985e6a701e20
Source dataset
uspto-grants-2003_04
Patent number
US06545009B1

Reaction notes

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