Chlorosuccinimide → HCID 89486058, compound

HRID 1469398Notes

Reaction equation

HRID 1469398 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1([C:13]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)=[O:14])SCCCS1.ClN1C(=[O:34])CCC1=O>C(#N)C.C(OCC)(=O)C.[N+]([O-])([O-])=O.[Ag+]>[O:34]=[C:7]([C:2]1[N:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:13]([CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)=[O:14]

Participants

6

Reactant 2

HCID 31398ChlorosuccinimideHCID 89486133HCID 89486133, compound

Product 1

HCID 89486058HCID 89486058, compound

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl 4-{[2-(pyrimidin-2-yl)-1,3-dithian-2-yl]carbonyl}piperidine-1-carboxylate (0.51 g, 1.24 mmol) in acetonitrile (10 ml) was added quickly to a well stirred solution of N-chlorosuccinimide (1.10 g, 8.24 mmol) and silver nitrate (1.54 g, 9.06 mmol) in aqueous 80% acetonitrile (30 ml) at room temperature. The mixture was stirred 10 min, then diluted with ethyl acetate, and washed successively with aqueous Na2S2O3 (2 N), 2 N sodium carbonate and brine. The organic layer was separated, dried (MgSO4) and concentrated. The resulting residue was purified on a silica gel column (ethyl acetate/hexane) to give the title compound. LC-MS m/e 320.15 [M+1]+.

Workup

  1. washwashed successively with aqueous Na2S2O3 (2 N), 2 N sodium carbonate and brine
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe resulting residue was purified on a silica gel column (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9bc2558478dc4eb697c6c187f3f98f0a
Source dataset
uspto-grants-2015_04
Patent number
US09006268B2

Reaction notes

Loading…