Acetic Anhydride → (E)-2-acetylamino-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-acrylic acid

HRID 2116678Notes

Reaction equation

[NH2:1][C:2]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[Cl:14].[C:15]([NH:18][CH2:19][C:20]([OH:22])=[O:21])(=[O:17])[CH3:16].C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>C1(C)C=CC=CC=1.O>[C:15]([NH:18]/[C:19](=[CH:6]/[C:5]1[CH:8]=[C:9]([C:10]([F:13])([F:12])[F:11])[C:2]([NH2:1])=[C:3]([Cl:14])[CH:4]=1)/[C:20]([OH:22])=[O:21])(=[O:17])[CH3:16]

Participants

Conditions

Temperature: 128 °C

Procedure

A mixture of 50.0 g (224 mmol) 4-amino-3-chloro-5-trifluoromethyl-benzaldehyde, 39.3 g (335 mmol) N-acetylglycine, 27.5 g (335 mmol) sodium acetate and 200 ml acetic anhydride was stirred for 2 hours in an oil bath at an oil bath temperature of 128° C. After cooling to an oil bath temperature of 90° C. 100 ml of water were added dropwise and the resulting suspension was added to a mixture of 1000 ml of water and 500 ml of toluene. The precipitate formed was suction filtered, washed with 300 ml of toluene and 500 ml of water and dried overnight at 60° C. in the circulating air dryer.

Workup

temperatureAfter cooling to an oil bath temperature of 90° C
customThe precipitate formed
filtrationfiltered
washwashed with 300 ml of toluene and 500 ml of water
customdried overnight at 60° C. in the circulating air dryer

Sources & evidence

ORD record: ord-10dfa442898848b5a73b028f43127b1b
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07439237B2

Reaction notes

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