1,3-Dimethyl-2-imidazolidinone → 4-Chloro-1-benzothiophene

HRID 1500542Notes

Reaction equation

C([C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([Cl:13])[C:6]=2[CH:5]=1)(O)=O.CN1CCN(C)C1=O.N12CCCN=C1CCCCC2>Cl>[Cl:13][C:12]1[C:6]2[CH:5]=[CH:4][S:8][C:7]=2[CH:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 177.5 °C

Procedure

A mixture of 2-carboxy-4-chlorobenzo[b]thiophene (50.00 g), 1,3-dimethyl-2-imidazolidinone (DMI; 200 ml), and 1,8-diazabicyclo[5.4.0]-undec-7-ene (140.7 ml) was heated at 160 to 195° C. with stirring for 6 hours. After the mixture was cooled to 10° C., the mixture was added to 3N-hydrochloric acid (350 ml) cooled to 10° C. After the mixture was extracted with toluene (500 ml), the toluene layer was washed with 3N-hydrochloric acid, water, aqueous sodium bicarbonate solution, water, saline, and water in this order, and then concentrated to obtain 4-chlorobenzo[b]thiophene.

Workup

temperatureAfter the mixture was cooled to 10° C.
temperaturecooled to 10° C
extractionAfter the mixture was extracted with toluene (500 ml)
washthe toluene layer was washed with 3N-hydrochloric acid, water, aqueous sodium bicarbonate solution, water, saline, and water in this order
concentrationconcentrated

Sources & evidence

ORD record: ord-6cef58642c844d109c5ed65120839b76
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206169B2

Reaction notes

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