Imidazole → HCID 58097285, compound

HRID 1514754Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[S:17][CH2:18][CH2:19][OH:20])=[N:9][N:10]=2)[CH:7]=1.N1C=CN=C1.CN(C1C=CC=CN=1)C.Cl[Si:36]([CH:43]([CH3:45])[CH3:44])([CH:40]([CH3:42])[CH3:41])[CH:37]([CH3:39])[CH3:38]>CC1CCCO1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[S:17][CH2:18][CH2:19][O:20][Si:36]([CH:43]([CH3:45])[CH3:44])([CH:40]([CH3:42])[CH3:41])[CH:37]([CH3:39])[CH3:38])=[N:9][N:10]=2)[CH:7]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a slurry of alcohol of Example 6 (51.3 g, 0.146 moles) in 2-methyltetrahydrofuran (257 ml) was added imidazole (11.9 g, 0.175 moles) and dimethylaminopyridine (1.79 g, 0.015 moles). Chlorotriisopropylsilane (33.9 g, 0.175 moles) was added over 10 minutes and the resultant mixture heated at 50° C. for 18 hours. The reaction was cooled to 20° C. and washed with 1M hydrochloric acid solution (257 ml) and the aqueous extracted with 2-methyltetrahydrofuran (103 ml). The combined organics were washed with 10% w/w sodium chloride solution, then distilled under reduced pressure, and replaced with n-heptane to give a final volume of 513 ml. The resultant slurry was cooled to 5° C. and granulated for 18 hours. The solid was collected by filtration to give the title compound as a white solid (63.0 g, 87%).

Workup

washwashed with 1M hydrochloric acid solution (257 ml)
extractionthe aqueous extracted with 2-methyltetrahydrofuran (103 ml)
washThe combined organics were washed with 10% w/w sodium chloride solution
distillationdistilled under reduced pressure
customto give a final volume of 513 ml
temperatureThe resultant slurry was cooled to 5° C.
filtrationThe solid was collected by filtration

Sources & evidence

ORD record: ord-193d493a7ba74cd7ac3acea58c832596
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222273B2

Reaction notes

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