Hydrochloric Acid → 3-Fluoro-4-(6-(1-phenylcyclopropyl)benzo[d]thiazol-2-yl)benzaldehyde

HRID 1177445Notes

Reaction equation

[O:1]1CCCO[CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[CH:21]=[C:20]([C:22]4([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[CH2:24][CH2:23]4)[CH:19]=[CH:18][C:16]=3[N:17]=2)=[C:9]([F:31])[CH:8]=1.Cl>C1COCC1>[F:31][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[C:13]1[S:14][C:15]2[CH:21]=[C:20]([C:22]3([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:23][CH2:24]3)[CH:19]=[CH:18][C:16]=2[N:17]=1)[CH:2]=[O:1]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-(1-phenylcyclopropyl)-benzo[d]thiazole (0.061 g, 0.14 mmol) and 5N HCl (3.50 mL, 0.14 mmol) in THF (7.0 mL) was heated to 70° C. for 3 h. The reaction was cooled and concentrated in vacuo, placed in an ice bath, and basified with 5 N aq. NaOH. The solid was collected by filtration, rinsed with water and MeOH, and was dried in vacuo to afford 3-fluoro-4-(6-(1-phenylcyclopropyl)-benzo[d]thiazol-2-yl)benzaldehyde. MS (ESI) m/z: Calculated: 373.1; Observed: 374.0 (M++1).

Workup

temperatureThe reaction was cooled
concentrationconcentrated in vacuo
customplaced in an ice bath
filtrationThe solid was collected by filtration
washrinsed with water and MeOH
customwas dried in vacuo

Sources & evidence

ORD record: ord-7d7204a4a14d44f9bc45c82c9b37cabb
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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