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

HRID 1508071Notes

Reaction equation

HRID 1508071 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

4

Reactant 2

HCID 67184N-bromobutanimideHCID 589943702-(4-Amino-phenyl)-ethanesulfonic acid dimethylamide

Product 1

HCID 589943492-(4-Amino-3-bromo-phenyl)-ethanesulfonic acid dimethylamideYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

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

Sources & evidence

ORD record
ord-552b4eba91a748ee80e4122ac3e91fe1
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

Loading…