Hydrochloric Acid → HCID 51349215, compound

HRID 401095Notes

Reaction equation

[OH:1][C:2]1[C:9]([O:10][CH2:11][CH2:12][CH3:13])=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[C:17]1([C:23](=O)[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[NH2:32][C:33]([NH2:35])=[O:34].Cl>C(O)C>[OH:1][C:2]1[C:9]([O:10][CH2:11][CH2:12][CH3:13])=[CH:8][C:5]([CH:6]2[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[NH:35][C:33](=[O:34])[NH:32]2)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15]

Participants

Conditions

Temperature: 110 °C

Procedure

The mixture of 4-hydroxy-3-nitro-5-propoxybenzaldehyde (Intermediate 65) (126 mg, 0.56 mmol), 1,2-diphenylethanone (131 mg, 0.672 mmol), urea (100 mg, 1.68 mmol) and concentrated hydrochloric acid (0.1 mL) in ethanol (5 mL) was stirred at reflux (110° C.) under N2 overnight. The reaction was concentrated and purified by silica gel column chromatography, followed by preparative HPLC to give Compound 130 (27 mg, yield 10.8%) as a solid. 1H NMR (DMSO-d6 400 MHz): δ 10.27 (s, 1H), 8.72 (d, J=1.6 Hz, 1H), 7.54 (s, 1H), 7.45 (d, J=2.0 Hz, 1H), 7.18-7.27 (m, 6H), 7.00-7.06 (m, 3H), 6.82-6.84 (m, 2H), 5.197 (d, J=2.8 Hz, 1H), 3.90-3.97 (m, 2H), 1.71-1.76 (m, 2H), 0.970 (t, J=7.6 Hz, 3H); MS (ESI): m/z 446.3 [M+1]+.

Workup

concentrationThe reaction was concentrated
custompurified by silica gel column chromatography

Sources & evidence

ORD record: ord-59e59b429e6249c289e431af2e434cab
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741915B2

Reaction notes

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