Sodium Bicarbonate → HCID 58746450, compound

HRID 724592Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([S:15]([NH2:18])(=[O:17])=[O:16])[CH:10]=2)=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].[C:24]([OH:27])(=[S:26])[CH3:25]>C(#N)C>[S:15]([C:11]1[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][S:26][C:24](=[O:27])[CH3:25])=[CH:4][CH:5]=2)[CH:14]=[CH:13][CH:12]=1)(=[O:17])(=[O:16])[NH2:18]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 4′-(bromomethyl)biphenyl-3-sulfonamide (1.28 g, 3.9 mmol) (WO 01/70753) in acetonitrile (16.4 mL) was treated with sodium bicarbonate (475 mg, 5.7 mmol) and thioacetic acid (0.34 mL, 4.7 mmol). The reaction mixture was stirred at 25° C. for 16 h. Additional sodium bicarbonate and thioacetic acid (0.4 eq. each) were added followed by acetonitrile (5 mL) and the reaction mixture was heated to 50° C. for 30 min. The reaction mixture was washed with water (10 mL) and brine (10 mL), dried with MgSO4, filtered, and concentrated to give a crude residue (quantitative) which was used in the next step without further purification. 1H NMR (500 MHz, CDCl3): δ 8.15 (dd, J=2.0, 2.0 Hz, 1H), 7.92 (ddd, J=7.8, 2.0, 1.0 Hz, 1H), 7.80 (ddd, J=7.8, 2.0, 1.0 Hz, 1H), 7.61 (dd, J=7.8, 7.8 Hz, 1H), 7.58–7.55 (m, 2H), 7.44–7.41 (m, 2H), 4.90 (br s, 2H), 4.19 (s, 2H), 2.40 (s, 3H); LCMS found for C15H15NO3S2Na (M+Na)+: m/z=344.

Workup

temperaturethe reaction mixture was heated to 50° C. for 30 min
washThe reaction mixture was washed with water (10 mL) and brine (10 mL)
dry with materialdried with MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-c3d89fcec24e4c8abcec81d1ad0d9730
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141596B2

Reaction notes

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