Benzenesulfonyl chloride → 2-Benzenesulfonyl-5,6,7,8-tetrahydro-4H-thieno[2,3-d]azepine

HRID 1365609Notes

Reaction equation

C(OC([N:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[CH:14][S:15][C:9]=2[CH2:8][CH2:7]1)=O)C.[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[C:16]1([S:22]([C:14]2[S:15][C:9]3[CH2:8][CH2:7][NH:6][CH2:12][CH2:11][C:10]=3[CH:13]=2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The product of Example 1, step (d) (75 mg, 0.33 mmol) was dissolved in 2 mL DCE and treated with phenyl sulfonyl chloride (83 μL, 0.66 mmol) followed by AlCl3 (88 mg, 0.66 mmol). After heating to 80° C. for ½ hour, the reaction was cooled and quenched carefully with 1 M NaOH. The product was extracted into DCM (2×). The organic extracts were concentrated and the residue was dissolved in 3 mL each EtOH and 40% aqueous KOH. The reaction was heated to 100° C. for 14 hours, cooled, and diluted with water. The title compound was extracted into DCM (2×5 mL) and purified by preparative HPLC-MS. 1H NMR (CD3OD) δ 7.96 (d, J=8.1 Hz, 2H), 7.67-7.56 (m, 3H), 5.56 (s, 1H), 3.38-3.32 (m, 4H), 3.27-3.23 (m, 2H), 3.09 (t, J=5.4 Hz, 2H); MS: ESI (positive): 294 (M+H).

Workup

temperaturethe reaction was cooled
customquenched carefully with 1 M NaOH
extractionThe product was extracted into DCM (2×)
concentrationThe organic extracts were concentrated
dissolutionthe residue was dissolved in 3 mL each EtOH
temperatureThe reaction was heated to 100° C. for 14 hours
temperaturecooled
additiondiluted with water
extractionThe title compound was extracted into DCM (2×5 mL)
custompurified by preparative HPLC-MS

Sources & evidence

ORD record: ord-b1ea907671e74dfcbd6b191861706774
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893051B2

Reaction notes

Loading…