Maleic Anhydride → 3-(4-Cyano-3-trifluoromethylphenylcarbamoyl)acrylic acid

HRID 966937Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]#[N:13])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(OCCCC)(=O)C.[C:22]1(=[O:28])[O:27][C:25](=[O:26])[CH:24]=[CH:23]1>CCCCCCC>[C:12]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:22]([CH:23]=[CH:24][C:25]([OH:27])=[O:26])=[O:28])=[CH:7][C:6]=1[C:8]([F:9])([F:10])[F:11])#[N:13]

Participants

Conditions

Temperature: 60 °C

Procedure

5-amino-2-cyanobenzotrifluoride (210.6 mmoles; 40.00 g) and butyl acetate (80 mL) were added to a 250 mL round bottom flask, followed by the addition of maleic anhydride (231.9 mmoles, 23.20 g). The resulting suspension was heated to 60° C. for 3.5 h. The reaction mixture was cooled to 25° C. and then heptane (160 mL) was added dropwise over a period of 25 minutes. The resulting suspension was filtered and washed with a mixture of 4:1, hepatane:butyl acetate (30 mL) and heptane (45 mL). The cake was dried in vacuo to give 60 g (95% yield) of compound 516A.

Workup

temperatureThe reaction mixture was cooled to 25° C.
filtrationThe resulting suspension was filtered
washwashed with a mixture of 4:1, hepatane
customThe cake was dried in vacuo

Sources & evidence

ORD record: ord-b3956c5490ac41dc80c1192e12a606f9
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06953679B2

Reaction notes

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