Sodium hydride → Isopropyl 2-chloro-4-fluoro-5-{3-[2-(ethoxycarbonyl)-1-trifluoromethyl-vinyl]ureido}benzoate

HRID 1193921Notes

Reaction equation

[NH2:1]/[C:2](/[C:9]([F:12])([F:11])[F:10])=[CH:3]\[C:4]([O:6][CH2:7][CH3:8])=[O:5].[H-].[Na+].[Cl:15][C:16]1[CH:27]=[C:26]([F:28])[C:25]([N:29]=[C:30]=[O:31])=[CH:24][C:17]=1[C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19]>CCCCCC.CN(C)C=O>[Cl:15][C:16]1[CH:27]=[C:26]([F:28])[C:25]([NH:29][C:30]([NH:1][C:2]([C:9]([F:10])([F:11])[F:12])=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:31])=[CH:24][C:17]=1[C:18]([O:20][CH:21]([CH3:22])[CH3:23])=[O:19]

Participants

Conditions

Temperature: -15 °C

Procedure

A solution of 3.55 g of ethyl 3-amino-4,4,4-trifluorocrotonate in 50 ml of n-hexane is added dropwise while stirring at 0°-3° C. during 15 minutes to 0.85 g of a 55% sodium hydride dispersion in 50 ml of dimethylformamide and the mixture is stirred for 30 minutes. A solution of 5.0 g of isopropyl 2-chloro-4-fluoro-5-isocyanatobenzoate in 100 ml of n-hexane is subsequently added dropwise during 5 minutes while stirring and cooling at -15° C. The temperature of the reaction mixture rises to 10° C. and the mixture is thereafter stirred at room temperature for one hour. The intermediate isopropyl 2-chloro-4-fluoro-5-[3-(2-ethoxycarbonyl -1-trifluoromethyl-vinyl)ureido]-benzoate which thereby separates is not isolated.

Workup

stirringwhile stirring
customrises to 10° C.
stirringthe mixture is thereafter stirred at room temperature for one hour

Sources & evidence

ORD record: ord-89a4946fbc29455194e14239a0e391e7
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04812164

Reaction notes

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