Ethanolamine → N-hydroxyethyl-2-amino-3-methyl-5-chlorobenzamide

HRID 623281Notes

Reaction equation

CO[C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[NH2:12].[CH2:14]([CH2:16][NH2:17])[OH:15]>C(#N)C>[OH:15][CH2:14][CH2:16][NH:17][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[NH2:12]

Participants

Conditions

Temperature: 70 °C

Procedure

To a 100 mL round-bottom flask, 0.1 mol of 2-amino-3-methyl-5-chlorobenzoic acid methyl ester having the structural formula of VIII-3, 100 mL of acetonitrile, 0.4 mol of ethanolamine were added, heated to 70° C. and reacted for 3 hours, after treatment 20.2 grams of N-hydroxyethyl-2-amino-3-methyl-5-chlorobenzamide having a structural formula of III-3 was obtained, and the yield was 88.4%; To a 50 mL round-bottom flask, 3.0 mmol of N-hydroxyethyl-2-amino-3-methyl-5-chlorobenzamide having the structural formula of III-3, 3.0 mmol of 1-(3,5-dichloropyridine-2-yl)-3-bromo-1H-pyrazole-5-carboxylic acid having a structural formula of II-3, 10 mL of acetonitrile were added, and 9.0 mmol of potassium carbonate and 0.2 gram of potassium iodide were added under stirring, cooled to −7° C. and a 3 mL acetonitrile solution of 12 mmol methanesulfonyl chloride was dripped, after dripping was completed reacted at 0° C. for 1.0 hour, reacted at 20° C. for 1.0 hour, 10 mL of water was added and stirred for 0.5 hour, filtered and dried to obtain 1.52 grams of 1-(3,5-dichloropyridine-2-yl)-3-bromo-N-(2-methyl-4-chloro-6-hydroxyethylaminocarbonyl)phenyl-1H-pyrazole-5-formamide having a structural formula of I-29 as a pale yellow solid, and the yield was 92.7%.

Workup

customreacted for 3 hours

Sources & evidence

ORD record: ord-cad7e4c87de1480ab289e9bc29c628a8
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09301529B2

Reaction notes

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