2,3,4,5-Tetrahydrobenzo[F][1,4]thiazepine 1,1-dioxide → 4-(4-Chloro-6-(trifluoromethoxy)quinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide

HRID 540108Notes

Reaction equation

Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][C:14]([F:17])([F:16])[F:15])[CH:8]=2)[N:3]=1.[S:18]1(=[O:30])(=[O:29])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH2:22][NH:21][CH2:20][CH2:19]1>C(O)CCC>[Cl:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][C:14]([F:17])([F:16])[F:15])[CH:8]=2)[N:3]=[C:2]([N:21]2[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[S:18](=[O:30])(=[O:29])[CH2:19][CH2:20]2)[CH:11]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2,4-dichloro-6-(trifluoromethoxy)quinoline (250 mg, 0.89 mmol), 2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide (210 mg, 1.06 mmol) and n-butanol (2 mL) was heated with stirring in a 5 mL of microwave process vial for 3 hours at 150° C. under microwave irradiation. The mixture was filtered. The formed solid was collected by filtration and washed with 10 mL of mixture solution of petroleum ether and ethyl acetate (V/V=10/1) to afford 0.3 g of the product (yield was 77%).

Workup

temperaturewas heated
filtrationThe mixture was filtered
filtrationThe formed solid was collected by filtration
washwashed with 10 mL of mixture solution of petroleum ether and ethyl acetate (V/V=10/1)

Sources & evidence

ORD record: ord-f869f477935f45f6a007826bc4f6b8fb
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871756B2

Reaction notes

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