Ethanol → ethyl N-(2,3-dihydrobenzofuran-7-yl)carbamate

HRID 440644Notes

Reaction equation

[NH2:1][C:2]1[C:10]2[O:9][C:8](C)(C)[CH2:7][C:6]=2[C:5](Cl)=[CH:4][CH:3]=1.Cl[C:15]([O:17][C:18](Cl)(Cl)Cl)=[O:16].[CH2:22](O)C>>[O:9]1[C:10]2[C:2]([NH:1][C:15](=[O:16])[O:17][CH2:18][CH3:22])=[CH:3][CH:4]=[CH:5][C:6]=2[CH2:7][CH2:8]1

Participants

Reactant 3

HCID 702Ethanol

HCID 10426Diphosgene

HCID 224047737-Amino-4-chloro-2,3-dihydro-2,2-dimethylbenzofuran

Product 1

HCID 22404805ethyl N-(2,3-dihydrobenzofuran-7-yl)carbamate

Procedure

Schema 4 illustrates an alternative process for preparing the uracils of this invention in which a 7-amino-2,3-dihydrobenzofurnan, for example, 7-amino-4-chloro-2,3-dihydro-2,2-dimethylbenzofuran, is successively treated with trichloromethyl chloroformate and then ethanol to give the corresponding ethyl N-(2,3-dihydrobenzofuran-7-yl)carbamate (X). The carbamate is then reacted with sodium hydride and a 3-amino-3-fluoroalkylacrylate, for example, ethyl 3-amino-4,4,4-trifluorocrotonate, and subsequently with an alkyl iodide and potassium carbonate to produce the 3-(2,3-dihydrobenzofuran-7-yl)-1-alkyl-6-haloalkyluracil, for example, 3-(4-chloro-2,3-dihydro-2,2-dimethylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (VI). The 3-(2,3-dihydrobenzofuran-3-on-7-yl)-1-alkyl-6-haloalkyluracils of this invention may be prepared using an analogous method.

Sources & evidence

ORD record: ord-07b67db57d8f4437bf4eb56b14796104
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05521147

Reaction notes

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