Anthranilamide → N-(2-carbamoylphenyl)-2-chloro-6-methoxybenzamide

HRID 2079305

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[C:13]=1[C:14](Cl)=[O:15]>N1C=CC=CC=1>[C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[NH:1][C:14](=[O:15])[C:13]1[C:17]([O:21][CH3:22])=[CH:18][CH:19]=[CH:20][C:12]=1[Cl:11])(=[O:5])[NH2:6]

Participants

Conditions

Temperature: 0 °C

Procedure

2-Amino-benzamide (6.9 g, 50.8 mmol) was dissolved in 50 mL of pyridine and cooled to 0° C. 2-Chloro-6-methoxy-benzoyl chloride was added dropwise to the solution. After complete addition, the reaction was left to stir at room temperature for three days, which resulted in formation of a brown, cloudy solution. The reaction mixture was then poured into 150 mL of ice water. The precipitate was filtered and washed twice with water, twice with THF and finally twice with CH2Cl2 to obtain N-(2-carbamoylphenyl)-2-chloro-6-methoxybenzamide (13.3 g, 43.7 mmol, 86%).

Workup

additionAfter complete addition
waitthe reaction was left
customwhich resulted in formation of a brown, cloudy solution
filtrationThe precipitate was filtered
washwashed twice with water, twice with THF and finally twice with CH2Cl2

Sources & evidence

ORD record: ord-f96f3f7a4f8c4759956386e625934998
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928107B2

Linked notes

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