2-Acetylthiophene → HCID 54249194, compound

HRID 1979799Notes

Reaction equation

[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6]CCCCC.[C:12]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)(=O)[CH3:13].[Cl-:20].[NH4+:21].C(O[CH:26]([CH3:28])[CH3:27])(C)C>O1CCCC1>[Cl:20][C:4]1[CH:3]=[CH:2][CH:1]=[CH:28][C:26]=1[CH:27]=[N:21][CH:13]=[C:12]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)[CH3:6]

Participants

Conditions

Temperature: -30 °C

Procedure

23.4 ml. of a 25% (w/w) solution of n-butyllithium in hexane (0.088 mol) are added, with stirring, at -78° C. and under nitrogen, to the imine prepared above (0.088 mol), dissolved in 100 ml. of anhydrous tetrahydrofuran. 11.1 g. (0.088 mol) 2-acetylthiophene in 20 ml. of tetrahydrofuran are added to the dark red solution at -78° C. The reaction mixture is stirred for 2 hours at -30° C. and then for 12 hours at ambient temperature, poured into a saturated aqueous solution of ammonium chloride and finally extracted 3 times with 100 ml. of methylene chloride. The combined organic phases are washed with water, dried over anhydrous sodium sulphate and evaporated to give an oily residue which solidifies upon trituration in diisopropyl ether to give 14.6 g. (yield: 63) 1-(2-chlorophenyl)-4-(thien-2-yl)-4-methyl-2-azabuta-1,3-diene in the form of yellow crystals giving a single spot in TLC; m.p. 102° C.

Workup

customprepared above (0.088 mol)
dissolutiondissolved in 100 ml
waitfor 12 hours at ambient temperature
extractionfinally extracted 3 times with 100 ml
washThe combined organic phases are washed with water
dry with materialdried over anhydrous sodium sulphate
customevaporated
customto give an oily residue which
customto give 14.6 g

Sources & evidence

ORD record: ord-406b1cab41af469080bf6c7270557599
Source dataset: uspto-grants-1984_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04482718

Reaction notes

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