Ethanolamine → 3-chloro-4-(2-hydroxyethylamino)-N-(3-hydroxy-4-methyl-phenyl)-benzamide

HRID 2426110Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1F)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([OH:15])[CH:9]=1)=[O:6].[CH2:20]([CH2:22][NH2:23])[OH:21]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[NH:23][CH2:22][CH2:20][OH:21])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([OH:15])[CH:9]=1)=[O:6]

Participants

Conditions

Temperature: 140 °C

Procedure

A solution of 3-chloro-4-fluoro-N-(3-hydroxy-4-methyl-phenyl)-benzamide (1.0 g, 3.58 mmol, from above) in dimethylsulfoxide (5.0 mL) was treated with ethanolamine (10.0 mL) (Aldrich) and heated at 140° C. for 50 minutes in a microwave reactor. The reaction mixture was then partitioned between ethyl acetate and water. The aqueous phase was acidified with 2N hydrochloric acid. The precipitate was filtered, washed with water and dried. The aqueous phase was extracted with ethyl acetate (2×). The combined organic phase was washed with water and brine, dried (magnesium sulfate) and concentrated. The two solid samples were combined and dried to give 3-chloro-4-(2-hydroxy-ethylamino)-N-(3-hydroxy-4-methyl-phenyl)-benzamide. (Yield 1.13 g).

Workup

customThe reaction mixture was then partitioned between ethyl acetate and water
filtrationThe precipitate was filtered
washwashed with water
customdried
extractionThe aqueous phase was extracted with ethyl acetate (2×)
washThe combined organic phase was washed with water and brine
dry with materialdried (magnesium sulfate)
concentrationconcentrated
customdried

Sources & evidence

ORD record: ord-85b7bb4162794ca892cc1f7b776d59ce
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968554B2

Reaction notes

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