Acetonitrile → 5-Formyl-4-chlorothiophene-3-carbonitrile

HRID 1582924Notes

Reaction equation

N(OC(C)(C)C)=O.N[C:9]1[S:10][C:11]([CH:17]=[O:18])=[C:12]([Cl:16])[C:13]=1[C:14]#[N:15].C(#N)C>CN(C)C=O>[CH:17]([C:11]1[S:10][CH:9]=[C:13]([C:14]#[N:15])[C:12]=1[Cl:16])=[O:18]

Participants

Conditions

Temperature: 25 °C

Procedure

35 g (325 mmol) of tert-butyl nitrite were added dropwise at room temperature to a solution of 53.0 g (250 mmol) of 2-amino-4-chloro-5-formylthiophene-3-carbonitrile (the synthesis of this compound is described in Patent DB 3738910) in 600 ml of a 1:1 mixture of acetonitrile and dimethylformamide, during which process the temperature of the reaction mixture rose from 20° C. to 37° C. and vigorous evolution of gas began. The mixture was cooled to 25° C. and stirred for 7 hours at room temperature, the black solution was concentrated on a rotary evaporator under a high vacuum, the residue was purified by column chromatography (eluant dichloromethane), and 29 g (68%) of the desired compound were obtained as yellow oil. 1H NMR (270 MHz, DMSO-d6): δ=9.1 (s, 1H), 10.0 (s, 1H).

Workup

customthe synthesis of this compound
customrose from 20° C. to 37° C.
concentrationthe black solution was concentrated on a rotary evaporator under a high vacuum
customthe residue was purified by column chromatography (eluant dichloromethane)

Sources & evidence

ORD record: ord-305eea2c6e2144cf9d61b01ea03bb2e8
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06740647B1

Reaction notes

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