Hydrochloric Acid → HCID 66987425, compound

HRID 2109499Notes

Reaction equation

[C:1]([NH:9][C:10](=[CH:15]N(C)C)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]1([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>C(O)(C)C>[C:1]([NH:9][C:10](=[CH:15][N:25]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 10 °C

Procedure

66 g (266 mmol) of methyl 2-benzoylamino-3-dimethylaminoacrylate and 50 g (295 mmol) of diphenylamine were dissolved at 40° C. in 1300 ml of isopropanol. The solution was admixed with 60 ml (725 mmol) of concentrated hydrochloric acid within 5 minutes (min) and stirred for a further 10 min. 550 ml of solvent were evaporated off under reduced pressure, the suspension was cooled to 10° C. and the crystallized product was filtered off. Yield: 83.5 g (84% of theory) 1H NMR: 3.62 (s, 3H), 6.95-7.10 (m, 6H), 7.20-7.30 (m, 8H), 7.32-7.40 (m, 1H), 7.61 (s, 1H), 8.70 (s, 1H)

Workup

custom550 ml of solvent were evaporated off under reduced pressure
filtrationthe crystallized product was filtered off

Sources & evidence

ORD record: ord-a646115012d342bebde7b3b5e4486a66
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514578B2

Reaction notes

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