Acetonitrile → HCID 90465074, compound

HRID 1424382Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:15]([O:16][CH3:17])=[CH:14][C:6]2[CH2:7][C:8](=[O:13])[NH:9][C:10](=[O:12])[CH2:11][C:5]=2[CH:4]=1.[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1.C([O-])([O-])=O.[K+].[K+].C(#N)C>ClCCl.O>[CH3:1][O:2][C:3]1[C:15]([O:16][CH3:17])=[CH:14][C:6]2[CH2:7][C:8](=[O:13])[N:9]([CH2:24][C:23]3[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=3)[C:10](=[O:12])[CH2:11][C:5]=2[CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3 g of 7,8-dimethoxy-1H-3-benzazepine-2,4(3H,5H)-dione (12.8 mmol), 2 g of 4-methoxy-benzyl chloride (12.8 mmol, 1 eq), 2.64 g of K2CO3 (19.1 mmol, 1.5 eq), 1.06 g of KI (6.4 mmol, 0.5 eq) and 30 mL of acetonitrile are introduced into a 100-mL three-necked flask. The reaction mixture is heated at 80° C. for 3 hours 30 minutes. 1 g of 4-methoxybenzyl chloride is introduced three times and the reaction mixture is held at 80° C. for 24 hours. After returning to ambient temperature, 30 mL of water and 30 mL of dichloromethane are introduced. After extraction and drying of the organic phase, the dark red oil obtained is purified by flash chromatography on a silica column (eluant: dichloromethane/methanol 99/1) to obtain the title product.

Workup

customAfter returning to ambient temperature
extractionAfter extraction
customdrying of the organic phase
customthe dark red oil obtained
customis purified by flash chromatography on a silica column (eluant: dichloromethane/methanol 99/1)

Sources & evidence

ORD record: ord-29c52a42ef4a4ae3950633e3edc1a75c
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927708B2

Reaction notes

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