Hydrochloric Acid → Ethyl [2-{2-chloro-4-fluoro-5-[2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}phenoxy]acetate

HRID 433729Notes

Reaction equation

[NH2:1]/[C:2](/[C:9]([F:12])([F:11])[F:10])=[CH:3]\[C:4]([O:6]CC)=O.[H-].[Na+].[Cl:15][C:16]1[CH:35]=[C:34]([F:36])[C:33]([NH:37][C:38](OCC)=[O:39])=[CH:32][C:17]=1[O:18][C:19]1[CH:31]=[CH:30][CH:29]=[CH:28][C:20]=1[O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].Cl>CN(C)C=O>[Cl:15][C:16]1[CH:35]=[C:34]([F:36])[C:33]([N:37]2[C:4](=[O:6])[CH:3]=[C:2]([C:9]([F:10])([F:11])[F:12])[NH:1][C:38]2=[O:39])=[CH:32][C:17]=1[O:18][C:19]1[CH:31]=[CH:30][CH:29]=[CH:28][C:20]=1[O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

To ethyl 3-amino-4,4,4-trifluorocrotonate are added N,N-dimethylformamide and sodium hydride and the mixture is stirred at 0° C. Thereafter, to the reaction solution is added a mixture of ethyl [2-(2-chloro-4-fluoro-5-ethoxycarbonylaminophenoxy)phenoxy]acetate [Intermediate compound A8-23] and N,N-dimethylformamide, and the mixture is stirred at 80° C. Then reaction solution is cooled to room temperature, then, poured into a mixture of hydrochloric acid and ice water, and the deposited crystal is collected by filtration to obtain ethyl [2-{2-chloro-5-[2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]-4-fluorophenoxy}phenoxy]acetate.s

Workup

additionThereafter, to the reaction solution is added
stirringthe mixture is stirred at 80° C
customThen reaction solution
temperatureis cooled to room temperature
filtrationthe deposited crystal is collected by filtration

Sources & evidence

ORD record: ord-6efad432ca2a41799598d9b974e9f6ad
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06667413B2

Reaction notes

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