Diisopropylethylamine → 4-bromo-2-methyl-N-(2-morpholin-4-yl-ethyl)benzene-sulfonamide

HRID 221869Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[C:4]([CH3:12])[CH:3]=1.[NH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(N(CC)C(C)C)(C)C>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)(=[O:10])=[O:9])=[C:4]([CH3:12])[CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 4-bromo-2-methylbenzene sulfonyl chloride (700 mg, 2.6 mmol), 4-(2-aminoethyl)morpholine (372 mg, 2.86 mmol, 1.1 eq), and N,N-diisopropylethylamine (1.0 mL, 5.71 mmol, 2.2 eq) in anhydrous tetrahydrofuran (13 mL, 0.2 M) was stirred at 40° C. under nitrogen for 18 h. Solvent was removed at reduced pressure and the residue was partitioned between EtOAc and water. The organic phase was washed with water and brine, dried over Na2SO4, and concentrated at reduced pressure. The residue was purified by MPLC (eluting with 50% to 75% EtOAc/hexane) to give 939 mg (99%) of the desired product as a white solid. 1H-NMR (DMSO-d6) δ 7.73 (d, J=8.4 Hz, 1H), 7.68 (broad s, 1H), 7.65 (dd, J=2.1, 0.6 Hz, 1H), 7.55 (ddd, J=7.3, 2.1, 0.6 Hz, 1H), 3.41 (t, J=4.5 Hz, 4H), 2.88 (t, J=6.3 Hz, 2H), 2.56 (s, 3H), 2.19 (t,=6.6 Hz, 2H), 2.16 to 2.12 (m, 4H); MS LC-MS [M+H]+=363 & 365, RT=1.90 min.

Workup

customSolvent was removed at reduced pressure
customthe residue was partitioned between EtOAc and water
washThe organic phase was washed with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated at reduced pressure
customThe residue was purified by MPLC (eluting with 50% to 75% EtOAc/hexane)

Sources & evidence

ORD record: ord-8fbdd4a246ef4f9c8e3e40cdbc1dd2f3
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207166B2

Reaction notes

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