N-bromobutanimide → HCID 21631631, compound

HRID 252810Notes

Reaction equation

HRID 252810 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[C:9]([O:13][C:14](=[O:29])[NH:15][C:16]1[C:20]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:19][S:18][CH:17]=1)([CH3:12])([CH3:11])[CH3:10]>C(Cl)(Cl)(Cl)Cl>[C:9]([O:13][C:14](=[O:29])[NH:15][C:16]1[C:20]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:19][S:18][C:17]=1[Br:8])([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 21794094HCID 21794094, compound

Product 1

HCID 21631631HCID 21631631, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

NBS (1.22 g, 6.87 mmol) was added to a solution of compound 57 (2.16 g, 6.87 mmol) in CCl4 (137 mL) at r.t. The mixture was stirred for 16 h. The solid material was filtered off and the filtrate was collected and washed with water. The organic layer was dried over MgSO4 and concentrated in vacuum. The residue was purified by flash chromatography with DCM as an eluent affording the title compound 58 (1.92 g, 71% yield). 1H NMR: (CDCl3) δ(ppm): 7.30 (bs, 1H), 6.00 (s, 1H), 1.45 (s, 9H), 1.43 (s, 9H). m/z: 415.4/417.4 (M+Na/M+2+Na). This procedure is essentially as described in Brugier et al., Tetrahedron, 56: 2985-2993 (2000), which is incorporated by reference in its entirety.

Workup

  1. filtrationThe solid material was filtered off
  2. customthe filtrate was collected
  3. washwashed with water
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuum
  6. customThe residue was purified by flash chromatography with DCM as an eluent

Sources & evidence

ORD record
ord-031e4b825a7f4c4ea089946696c604a9
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

Loading…