N-bromobutanimide → HCID 58994392, compound

HRID 1190151Notes

Reaction equation

HRID 1190151 reaction equation
[N:1]1([S:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C1C(=O)N([Br:25])C(=O)C1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:25][C:15]1[CH:16]=[C:11]([CH2:10][S:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)(=[O:9])=[O:8])[CH:12]=[CH:13][C:14]=1[NH2:17]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 29270684HCID 29270684, compound

Product 1

HCID 58994392HCID 58994392, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(morpholine-4-sulfonylmethyl)-phenylamine (437 mg, 1.70 mmol, WO 9720822) in DCM (10 mL) was added NBS (304 mg, 1.70 mmol) at 0° C. The solution was allowed to stir at RT for 15 min. Satd aq NaHCO3 (20 mL) was then added and the organic layer was separated, dried (Na2SO4) and concentrated to afford the title compound (564 mg, 98%). 1H-NMR (CDCl3; 400 MHz): δ 7.47 (d, 1H, J=1.9 Hz), 7.15 (dd, 1H, J=8.2, 1.9 Hz), 6.77 (d, 1H, J=8.2 Hz), 4.23 (br s, 2H), 4.12 (s, 2H), 3.65-3.68 (m, 4H), 3.14-3.17 (m, 4H).

Workup

  1. customthe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d185122f09854586a5f650e845523022
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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