Ethylamine → Allyl 2-(3-ethylureido)-5-(trifluoromethyl)benzoate

HRID 2225146Notes

Reaction equation

[NH2:1][C:2]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:3]=1[C:4]([O:6][CH2:7][CH:8]=[CH2:9])=[O:5].[C:18](Cl)(Cl)=[O:19].[CH2:22]([N:24](CC)CC)[CH3:23].C(N)C>C1COCC1.CCOC(C)=O>[CH2:22]([NH:24][C:18](=[O:19])[NH:1][C:2]1[CH:13]=[CH:12][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:10][C:3]=1[C:4]([O:6][CH2:7][CH:8]=[CH2:9])=[O:5])[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

Preparation B1, Step 2: The allyl 2-amino-5-(trifluoromethyl)benzoate from step 1 (ca. 15.7 mmol) was dissolved in THF (60 mL) and phosgene (24.9 mL, 47 mmol) was added at 0° C. dropwise. The reaction was stirred for 15 minutes at 0° C. Triethylamine (13.1 mL, 94 mmol) was slowly added and stirring was continued for 2 hours. The reaction was concentrated in vacuo to afford a yellow solid. A portion (2.4 g, ca. 7.7 mmol) of the yellow solid was dissolved in THF (40 mL) and the solution was charged with ethylamine (20 mL of a 2.0 M solution in THF). The reaction was stirred for 14 h at RT and then diluted with EtOAc. The organic phase was washed successively with 1N HCl (2×) and brine (1×) before being dried (Na2SO4), filtered, and concentrated in vacuo to give allyl 2-(3-ethylureido)-5-(trifluoromethyl)benzoate as a white solid (1.8 g). MS found: (M+Na)+=339.29.

Workup

stirringstirring
waitwas continued for 2 hours
concentrationThe reaction was concentrated in vacuo
customto afford a yellow solid
stirringThe reaction was stirred for 14 h at RT
washThe organic phase was washed successively with 1N HCl (2×) and brine (1×)
dry with materialbefore being dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-417deb89a1474015b28b6ef7093865d7
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378409B2

Reaction notes

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