N-bromobutanimide → 2-(4-Amino-3-bromo-phenyl)-ethanesulfonic acid dimethylamide

HRID 1190135Notes

Reaction equation

[CH3:1][N:2]([CH3:15])[S:3]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)(=[O:5])=[O:4].C1C(=O)N([Br:23])C(=O)C1>C(Cl)Cl>[CH3:15][N:2]([CH3:1])[S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[C:12]([Br:23])[CH:13]=1)(=[O:4])=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 737 mg (3.23 mmol) of 2-(4-amino-phenyl)-ethanesulfonic acid dimethylamide (as prepared in the previous step) in CH2Cl2 (20 mL) was cooled to 0° C. and treated with 574 mg (3.23 mmol) of NBS. The ice bath was removed and the mixture stirred at RT for 25 min. The mixture was diluted with CH2Cl2 (40 mL) and washed with saturated aqueous NaHCO3 (2×30 mL). The aqueous layer was extracted with CH2Cl2 (1×30 mL) the combined organic layers were dried (MgSO4) and concentrated in vacuo to afford 955 mg (96%) of the title compound as a white solid: 1H-NMR (CD3OD; 400 MHz): δ 7.35 (d, 1H, J=2.0 Hz), 7.04 (dd, 1H, J=8.0, 2.0 Hz), 4.44 (br s, 2H), 3.21-3.14 (m, 2H), 2.96-2.89 (m, 2H), 2.84 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C10H15N2OSBr, 307.0/309.0 (M+H). found 307.0/309.0.

Workup

customThe ice bath was removed
additionThe mixture was diluted with CH2Cl2 (40 mL)
washwashed with saturated aqueous NaHCO3 (2×30 mL)
extractionThe aqueous layer was extracted with CH2Cl2 (1×30 mL) the combined organic layers
dry with materialwere dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-adb0f76cd7a14b9ea003fec346e365bf
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674100B2

Reaction notes

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