Ethanol → HCID 15565693, compound

HRID 1990070Notes

Reaction equation

C(O)C.C(O[C:7](=[C:10]([C:13]#[N:14])[C:11]#[N:12])[CH2:8][CH3:9])C.[CH2:15]([O:17][C:18](=[O:21])[CH2:19][SH:20])[CH3:16].C([O-])(=O)C.[K+]>O>[CH2:15]([O:17][C:18]([C:19]1[S:20][C:7]([CH2:8][CH3:9])=[C:10]([C:11]#[N:12])[C:13]=1[NH2:14])=[O:21])[CH3:16]

Participants

Conditions

Temperature: 60 °C

Procedure

Ethanol, (11.0 L), 2-(1-ethoxy-propylidene)-malononitrile, (2.003 kg, 13.34 moles, 1.0 eq), ethyl-2-mercaptoacetate (1.652 kg, 13.34 moles, 1.0 eq.), and potassium acetate (1.983 kg, 20.0 moles, 1.5 eq.) are charged to a 22L 3-neck reaction flask equipped with an addition funnel, thermocouple, overhead stirrer, and condenser. The reaction mixture becomes dark red and exotherms to 72° C. The mixture is stirred for 1.25 hours while cooling to 60° C. Deionized water (2.6 L), is added to the reaction mixture over 30 minutes while cooling to 53° C. The reaction mixture is then cooled to 10° C. over 3.5 hours. The resulting suspension is filtered to recover the precipitate, and the filter cake is rinsed with a chilled mixture of 1.1 L ethanol and 3.9 L water. The filter cake is vacuum dried at room temperature, affording the title compound (2.552 kg) in 85.3% yield.

Workup

customequipped with an addition funnel
customexotherms to 72° C
temperaturewhile cooling to 53° C
temperatureThe reaction mixture is then cooled to 10° C. over 3.5 hours
filtrationThe resulting suspension is filtered
customto recover the precipitate
washthe filter cake is rinsed with a chilled mixture of 1.1 L ethanol and 3.9 L water
customdried at room temperature

Sources & evidence

ORD record: ord-a0d7f5c3c39c4f7ab199f4eb81e8fa1a
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642361B2

Reaction notes

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