Triethylamine → 3-Iodo-4-methyl-N-[3-(4-morpholinyl)phenyl]benzamide

HRID 31402

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5](Cl)=[O:6].C(N(CC)CC)C.[N:19]1([C:25]2[CH:26]=[C:27]([NH2:31])[CH:28]=[CH:29][CH:30]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CN(C)C=O>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:26]=1)=[O:6]

Participants

Conditions

Temperature: 80 °C

Procedure

3-Iodo4-methylbenzoyl chloride (Intermediate 1) (19.5 g, 69.6 mmol) was added portion-wise to a mixture of triethylamine (48 ml, 350 mmol) and 3-(4-morpholinyl)benzenamine (Intermediate 3) (12.6 g, 70.6 mmol) in dimethyl formamide (150 ml) and the mixture was heated at 80° C. for 16 hours. The solvent was removed in vacuo and the residue taken up in chloroform (200 ml). The organic layer was washed with water (2×100 ml), 2M sodium hydroxide solution (100 ml) and brine (100 ml), dried over magnesium sulfate, filtered and solvent removed in vacuo. The resulting yellow solid was titurated with diethyl ether and collected by filtration to yield the desired product as an off-white solid (20.0 g, 47.0 mmol). The product was used in subsequent reactions without further purification.

Workup

customThe solvent was removed in vacuo
washThe organic layer was washed with water (2×100 ml), 2M sodium hydroxide solution (100 ml) and brine (100 ml)
dry with materialdried over magnesium sulfate
filtrationfiltered
customsolvent removed in vacuo
filtrationcollected by filtration

Sources & evidence

ORD record: ord-a5cf4389c1a341c39cbf2e801622dc5c
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425555B2

Linked notes

Loading…