Thiourea → HCID 178490495, compound

HRID 633612Notes

Reaction equation

[NH2:1][C:2]([NH2:4])=[S:3].C[O-].[Na+:7].[CH3:8][O:9][C:10]1[C:29]([CH3:30])=[CH:28][C:13]([C:14]([NH:16][CH:17]([C:23](OCC)=[O:24])[C:18](OCC)=[O:19])=[O:15])=[CH:12][C:11]=1[CH3:31]>C(O)C>[OH:19][C:18]1[C:17]([NH:16][C:14](=[O:15])[C:13]2[CH:28]=[C:29]([CH3:30])[C:10]([O:9][CH3:8])=[C:11]([CH3:31])[CH:12]=2)=[C:23]([OH:24])[N:4]=[C:2]([S-:3])[N:1]=1.[Na+:7]

Participants

Conditions

Temperature: 60 °C

Procedure

20.6 g of thiourea were suspended in 900 ml of dry ethanol, and 75 ml of sodium methoxide solution (30% in methanol) were added. After 15 min, 91.0 g of diethyl 2-(4-methoxy-3,5-dimethylbenzoylamino)malonate were added a little at a time. Initially, this gave a clear solution, and soon a pale-yellow precipitate was formed. The reaction was then stirred at 60° C. for 3 hours. At room temperature, the precipitated solid was filtered off with suction and washed with about 100 ml of ethanol and then with diethyl ether, and dried under reduced pressure. This gave 78.3 g (84%) of the title compound which was reacted further without any further purification.

Workup

customInitially, this gave a clear solution
customsoon a pale-yellow precipitate was formed
filtrationAt room temperature, the precipitated solid was filtered off with suction
washwashed with about 100 ml of ethanol
dry with materialwith diethyl ether, and dried under reduced pressure
customThis gave 78.3 g (84%) of the title compound which was reacted further without any further purification

Sources & evidence

ORD record: ord-cf576cd0199f46359ae37a3ca92af595
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321787B2

Reaction notes

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