Water → Methyl 4-[(2-n-Butyl-5-formyl-4-iodo-1H-imidazol-5-yl)methyl]-1-naphthalene carboxylate

HRID 2347Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7]([C:11]1[NH:12][C:13]([CH:17]=[O:18])=[C:14]([I:16])[N:15]=1)[CH2:8][CH2:9][CH3:10].Br[CH2:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([C:31]([O:33][CH3:34])=[O:32])=[CH:23][CH:22]=1.O>CN(C)C=O>[CH2:7]([CH:11]1[N:15]=[C:14]([I:16])[C:13]([CH2:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]([C:31]([O:33][CH3:34])=[O:32])=[CH:23][CH:22]=2)([CH:17]=[O:18])[NH:12]1)[CH2:8][CH2:9][CH3:10]

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of 29.53 g (0.214 mol) of powdered potassium carbonate, 60.00 g (0.214 mol) of 2-butyl-4-iodoimidazole-5-carboxaldehyde, and 65.68 g (0.235 mol) of methyl 4-bromomethylnaphthalene-1-carboxylate (E. A. Dixon, A. Fischer, and F. P. Robinson, Can. J. Chem. 59, 2629 (1981)) in 600 ml of dimethylformamide was stirred for 5 hours under argon at 70° C. An additional 6.56 g (0.0235 mol) of the bromomethyl ester was added and the suspension was stirred an additional 15 hours at 70° C. The mixture was poured into water and the solid which separated was collected by filtration, washed with water, and triturated several times with 250 ml of boiling methanol to give 86.8 g (85%) of a solid; mp 177.5°-179° C.

Workup

customthe solid which separated
filtrationwas collected by filtration
washwashed with water
customtriturated several times with 250 ml of boiling methanol

Sources & evidence

ORD record: ord-ff9fddba17f84a17b2c77c4ed15d72d3
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05728842

Reaction notes

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