N-bromobutanimide → 2-Bromo-4-[2-(morpholine-4-sulfonyl)-ethyl]-phenylamine

HRID 1190126Notes

Reaction equation

[N:1]1([S:7]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C1C(=O)N([Br:26])C(=O)C1>C(Cl)Cl>[Br:26][C:16]1[CH:17]=[C:12]([CH2:11][CH2:10][S:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)(=[O:9])=[O:8])[CH:13]=[CH:14][C:15]=1[NH2:18]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 103 mg (0.381 mmol) of 4-[2-(morpholine-4-sulfonyl)-ethyl]-phenylamine (as prepared in the previous step) in CH2Cl2 (15 mL) was cooled to 0° C. and treated portionwise with 67.8 mg (0.381 mmol) of solid NBS. The mixture was stirred at 0° C. for 15 min, diluted with CH2Cl2 (30 mL) and washed with saturated aqueous NaHCO3 (1×20 mL). The organic layers were dried (MgSO4) and concentrated in vacuo to afford 133 mg (100%) of the title compound as a tan solid: Mass spectrum (ESI, m/z): Calcd. for C12H17N2O3SBr, 349.0/351.0 (M+H). found 348.7/350.8.

Workup

washwashed with saturated aqueous NaHCO3 (1×20 mL)
dry with materialThe organic layers were dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c5b34be7841144e8bd1780e76abd3dd2
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674100B2

Reaction notes

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