Toluene → HCID 10387616, compound

HRID 2081852Notes

Reaction equation

C(O[C:5]([C:17]1[N:21]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[C:20]([CH2:30][CH2:31][CH2:32][CH3:33])=[N:19][CH:18]=1)=[C:6](C1C=CN=CC=1)[C:7]([O:9][CH3:10])=[O:8])(=O)C.C1(C)C=CC=CC=1.N12C[CH2:50][CH2:49][N:48]=[C:47]1[CH2:46][CH2:45][CH2:44]CC2>CCOCC>[CH2:30]([C:20]1[N:21]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[C:17](/[CH:5]=[C:6](\[CH2:44][C:45]2[CH:46]=[CH:47][N:48]=[CH:49][CH:50]=2)/[C:7]([O:9][CH3:10])=[O:8])=[CH:18][N:19]=1)[CH2:31][CH2:32][CH3:33]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of methyl 3-acetoxy-3-[2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazol-5-yl]-2-(4-pyridyl)propenoate (7.5 mmol), toluene (50 mL) and 1,8-diazabicyclo[5,4,0]-undec-7-ene (DBU) (3.4 mL, 22.5 mmol) was heated at 90° C. for 18 hours under argon. The cooled mixture was diluted with ether, and washed with brine, dried and concentrated to 3.1 g (97%) of the title compound. NMR showed that the trans or E isomer was the primary product.

Workup

washwashed with brine
customdried
concentrationconcentrated to 3.1 g (97%) of the title compound

Sources & evidence

ORD record: ord-be57f97340a244de90df9805a292327b
Source dataset: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05185351

Reaction notes

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