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

HRID 1988874Notes

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=O)C>[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-Iodo-4-methylbenzoyl chloride (Intermediate 6) (19.5 g) was added portion-wise to a mixture of triethylamine (48 ml) and 3-(4-morpholinyl)benzenamine (Intermediate 8) (12.6 g) in DMF (150 ml) and the mixture was heated at 80° C. for 16 h. The solvent was removed under vacuum and the residue was dissolved 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 sulphate, filtered and concentrated under vacuum The resulting yellow solid was triturated with diethyl ether and collected by filtration to yield the title compound as an off-white solid (20.0 g). The product was used in subsequent reactions without further purification.

Workup

customThe solvent was removed under vacuum
dissolutionthe residue was dissolved in chloroform (200 ml)
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 sulphate
filtrationfiltered
concentrationconcentrated under vacuum The resulting yellow solid
customwas triturated with diethyl ether
filtrationcollected by filtration

Sources & evidence

ORD record: ord-ef3be8a465a94d978fa7fdbe4ba68d92
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642276B2

Reaction notes

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