Hydrochloric Acid → HCID 178526697, compound

HRID 1261227Notes

Reaction equation

[F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]=[CH:16][N:17](COCC[Si](C)(C)C)[CH:18]=3)[S:13][C:6]=12.Cl>CCO>[F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]=[CH:16][NH:17][CH:18]=3)[S:13][C:6]=12

Participants

Conditions

Temperature: 85 °C

Procedure

To a suspension of 92 (3.3 g, 6.8 mmol) in EtOH (8 ml) was added concentrated HCl (7 ml) and distilled water (4 ml). The mixture was heated at 80-90° C. for 2.5 h, cooled to room temperature and concentrated under reduced pressure. The remaining residue was subjected to azeotropic distillation with EtOH followed by neutralization with saturated aqueous NaHCO3. The solid that precipitated was filtered and washed with water, and the filtrate was extracted with EtOAc. The solid and EtOAc extract were combined, evaporated under reduced pressure and the residue was collected and dried to afford the title compound 93 (2.4 g, 100% yield) as a yellow solid. MS (m/z) 357.0 (M+H).

Workup

distillationdistilled water (4 ml)
temperaturecooled to room temperature
concentrationconcentrated under reduced pressure
distillationThe remaining residue was subjected to azeotropic distillation with EtOH
customThe solid that precipitated
filtrationwas filtered
washwashed with water
extractionthe filtrate was extracted with EtOAc
extractionThe solid and EtOAc extract
customevaporated under reduced pressure
customthe residue was collected
customdried

Sources & evidence

ORD record: ord-a75e6aea550443439fd554a147c1009e
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470850B2

Reaction notes

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