Chlorosuccinimide → HCID 67199636, compound

HRID 1408514Notes

Reaction equation

HRID 1408514 reaction equation
[CH:1]1([C:4]2[CH:8]=[C:7]([CH:9]3[CH2:11][CH2:10]3)[N:6]([C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=3[F:21])[N:5]=2)[CH2:3][CH2:2]1.[Cl:22]N1C(=O)CCC1=O>CN(C=O)C>[Cl:22][C:8]1[C:4]([CH:1]2[CH2:2][CH2:3]2)=[N:5][N:6]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=2[F:21])[C:7]=1[CH:9]1[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 67114771HCID 67114771, compound

Product 1

HCID 67199636HCID 67199636, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Intermediate 10 (1.15 g, 3.40 mmol) was dissolved in DMF and to this N-Chlorosuccinimide (0.64 g, 4.8 mmol) was added at 0° C. Then reaction was allowed to stir at rt for 2 h. After completion of the reaction, work up (EtOAc) and purification afforded the title compound (0.575 g). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.18-8.09 (m, 2H), 7.64 (t, J 8.3, 1H), 1.98-1.90 (m, 1H), 1.82-1.72 (m, 1H), 0.90-0.80 (m, 4H), 0.68-0.60 (m, 4H).

Workup

  1. additionwas added at 0° C
  2. customThen reaction
  3. customAfter completion of the reaction, work
  4. customup (EtOAc) and purification

Sources & evidence

ORD record
ord-a628ac02987141e08a541aae1d656beb
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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