Chlorosuccinimide → HCID 59644362, compound

HRID 1594525Notes

Reaction equation

HRID 1594525 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:4]=1[NH2:5].[Cl:13]N1C(=O)CCC1=O>CC#N>[Cl:13][C:8]1[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:4]([NH2:5])=[C:3]([O:2][CH3:1])[CH:9]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 854916-Nitro-o-anisidine

Product 1

HCID 59644362HCID 59644362, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the title compound of Example 21, Step A (26.6 mmol, 4.5 g) in MeCN (30 mL) at 60° C. was added N-chlorosuccinimide (29 mmol, 3.9 g). The solution was brought to reflux for 2 h and allowed to stand at ambient temperature for 16 h. The reaction mixture was partitioned between CH2Cl2 and saturated NaHCO3. The organic phase was washed with brine, dried with Na2SO4, and concentrated in vacuo to afford the product as a brown solid. LC-MS (ESI, Method B): 2.14 min, m/z 203.11 (M+1).

Workup

  1. temperatureto reflux for 2 h
  2. customThe reaction mixture was partitioned between CH2Cl2 and saturated NaHCO3
  3. washThe organic phase was washed with brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d25575a282648ddbb16eef806137c75
Source dataset
uspto-grants-2007_11
Patent number
US07301036B2

Reaction notes

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