Hydrochloric Acid → HCID 19790386, compound

HRID 1656136Notes

Reaction equation

C(N(C(C)C)CC)(C)C.[C:10]([CH2:12][C:13]([O:15][CH3:16])=[O:14])#[N:11].Br[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)=[O:20].Cl>O1CCCC1>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:19]([CH2:18][CH:12]([C:10]#[N:11])[C:13]([O:15][CH3:16])=[O:14])=[O:20])=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Diisopropylethyl amine (15.5 g, 0.12 mol) is added to dry tetrahydrofuran (60 mL) followed by a solution of methyl cyanoacetate (5.4 g, 0.055 mol) in tetrahydrofuran (10 mL). Finally, a solution of α-bromo-p-chloroacetophenone (11.0 g, 0.05 mol) in tetrahydrofuran (50 mL) is added. After three hours at room temperature, TLC (75/25 hexanes/ethyl acetate) indicates very little starting material. The reaction mixture is then heated at 50° C. for fifteen minutes, cooled and filtered. The filtrate is concentrated in vacuo to obtain an oil which solidifies when treated with dilute hydrochloric acid. The supernatant is decanted and the residue is taken up in ethyl acetate and dried. Work-up leaves a brown waxy solid (8.0 g, 64% crude yield) which on recrystallization from methanol gives the title compound as a white solid (4.3 g, mp 75°-79° C.).

Workup

temperaturecooled
filtrationfiltered
concentrationThe filtrate is concentrated in vacuo
customto obtain an oil which
customThe supernatant is decanted
customdried
customWork-up leaves a brown waxy solid (8.0 g, 64% crude yield) which
customon recrystallization from methanol

Sources & evidence

ORD record: ord-0d1f02ea21d14772ac5a315771ee7c17
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05252746

Reaction notes

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