Hydrochloric Acid → HCID 68576299, compound

HRID 2246046Notes

Reaction equation

CC(C)([O-])C.[K+].C1(C(C2C=CC=CC=2)=[N:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])C=CC=CC=1.[CH3:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30]([Cl:32])=[O:31].Cl>C1COCC1>[ClH:32].[NH2:14][CH:15]([C:30](=[O:31])[C:29]1[CH:33]=[CH:34][CH:35]=[CH:36][C:28]=1[CH3:27])[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

Conditions

Temperature: -78 °C

Procedure

Under nitrogen, 4.2 g (0.038 mol) of potassium tert-butoxide were suspended in THF. The mixture was cooled to −78° C., and 10.0 g (0.037 mol) of ethyl N-(diphenylmethylene)glycinate, dissolved in THF, were added dropwise. After 40 min at −78° C., the solution was transferred into a cooled dropping funnel (−78° C.) and added dropwise to a solution, cooled to −78° C., of 2-methylbenzoyl chloride in THF. After 1 h of stirring at −78° C., the reaction mixture was allowed to warm to 0° C. over a period of 2 h. The mixture was hydrolyzed using 10% strength hydrochloric acid, and stirring was continued. The solvents were removed and the residue was taken up in water and washed with MTBE. The aqueous phase was concentrated, methanol was added to the residue and the mixture was filtered. Concentration of the filtrate gave 6.2 g of the title compound as a colorless oil.

Workup

additionwere added dropwise
customthe solution was transferred into a cooled dropping funnel
addition(−78° C.) and added dropwise to a solution
temperatureto warm to 0° C. over a period of 2 h
stirringstirring
customThe solvents were removed
washwashed with MTBE
concentrationThe aqueous phase was concentrated
additionmethanol was added to the residue
filtrationthe mixture was filtered

Sources & evidence

ORD record: ord-de3bdf9bb9cd423bb0e262922372c6cb
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687435B2

Reaction notes

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