Chloroform → Morpholine-4-carboxylic acid (4-bromo-2-dimethylcarbamoyl-phenyl)-amide

HRID 2234651Notes

Reaction equation

[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].C(N(C(C)C)CC)(C)C.[N:23]1([C:29](Cl)=[O:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.C(Cl)(Cl)Cl>O>[Br:13][C:10]1[CH:11]=[CH:12][C:2]([NH:1][C:29]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:30])=[C:3]([C:4](=[O:5])[N:6]([CH3:7])[CH3:8])[CH:9]=1

Participants

Conditions

Temperature: 50 °C

Procedure

2-Amino-5-bromo-N,N-dimethyl-benzamide (2.00 g, 8.22 mmol), diisopropylethylamine (6.5 ml, 37.32 mmol), 4-morpholinecarbonyl chloride (4.3 ml, 37.46 mmol), and chloroform (20 ml) were combined and stirred for 18 hours at 50° C. Water was added to the mixture, and the organic layer was extracted. The organic layer was dried over sodium sulfate, concentrated in vacuo, and the crude material was purified by flash chromatography (50% to 100% ethyl acetate in hexanes) to give 1.13 g (39%) of morpholine-4-carboxylic acid (4-bromo-2-dimethylcarbamoyl-phenyl)-amide. 1H-NMR (250 MHz, DMSO-d6) δ 8.67 (s, 1H), 7.56-7.45 (m, 2H), 7.42 (t, J=9.3 Hz, 4H), 3.35-3.28 (m, 4H), 2.96-2.86 (m, 6H); MS: m/z 356.0+358.1 (M+H+).

Workup

extractionthe organic layer was extracted
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated in vacuo
customthe crude material was purified by flash chromatography (50% to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-d026034da3d94ea2800f67e2c017c5f5
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709645B2

Reaction notes

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