4-(1,3-Dioxolan-2-yl)benzonitrile → HCID 22502706, compound

HRID 1006942Notes

Reaction equation

[CH3:1][NH:2][C:3]([C:5]1[CH:9]=[CH:8][S:7][C:6]=1[CH3:10])=[O:4].C([Li])CCC.[O:16]1[CH2:20][CH2:19][O:18][CH:17]1[C:21]1[CH:28]=[CH:27][C:24](C#N)=[CH:23][CH:22]=1>O1CCCC1>[O:16]1[CH2:20][CH2:19][O:18][CH:17]1[C:21]1[CH:28]=[CH:27][C:24]([C:1]2[NH:2][C:3](=[O:4])[C:5]3[CH:9]=[CH:8][S:7][C:6]=3[CH:10]=2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: -70 °C

Procedure

To a solution of N-methyl-2-methylthiophene-3-carboxamide (18.5 g) in tetrahydrofuran (350 ml) was dropwise added 2.5M n-butyl lithium (100 ml) at −70° C. The resulting solution was stirred at −70° C. for 1.5 hr, followed by the addition of a solution of 4-(1,3-dioxolan-2-yl)benzonitrile (20.9 g) in tetrahydrofuran (100 ml) at once. After the dry ice/acetone bath was removed, the reaction mixture was back to room temperature. Three hours later, an aqueous solution of saturated ammonium chloride was added thereto, and the organic layer was separated, washed with water and dried. The filtrate was concentrated, and the resulting solid was washed with ethyl acetate, tetrahydrofuran/ether and n-hexane in this order. The resulting solid was then dried, to give the title compound as white crystals (6.24 g, yield; 31.7%).

Workup

customat −70° C
customAfter the dry ice/acetone bath was removed
customwas back to room temperature
additionThree hours later, an aqueous solution of saturated ammonium chloride was added
customthe organic layer was separated
washwashed with water
customdried
concentrationThe filtrate was concentrated
washthe resulting solid was washed with ethyl acetate, tetrahydrofuran/ether and n-hexane in this order
customThe resulting solid was then dried

Sources & evidence

ORD record: ord-86482fc44feb42a6b9d5b970ebfb4391
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06790844B2

Reaction notes

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