N-bromobutanimide → HCID 86699299, compound

HRID 331084Notes

Reaction equation

HRID 331084 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[C:14]3[C:24](=[O:25])[NH:23][CH:22]=[CH:21][C:15]=3[N:16]=[C:17]([S:19][CH3:20])[N:18]=2)=[CH:8][CH:7]=1.[Br:29]N1C(=O)CCC1=O>CN(C=O)C>[Br:29][C:21]1[C:15]2[N:16]=[C:17]([S:19][CH3:20])[N:18]=[C:13]([NH:12][C:9]3[CH:8]=[CH:7][C:6]([O:5][C:4]4[CH:26]=[CH:27][CH:28]=[C:2]([F:1])[CH:3]=4)=[CH:11][CH:10]=3)[C:14]=2[C:24](=[O:25])[NH:23][CH:22]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86699300HCID 86699300, compound

Product 1

HCID 86699299HCID 86699299, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 40 mL reaction vial was charged with 238d, (1.00 g, 2.53 mmol) in 15 mL of DMF. The mixture was gently heated until it became a clear solution, and allowed to cool down to room temperature. To the mixture was added N-bromosuccinimide (NBS, 498 mg, 2.80 mmol) and stirred for 1 h at rt. The solvent was removed under reduced pressure yielding the orange solid. The resulting solids were collected by filtration and washed acetonitrile to provide 1.04 g (87%) of the desired product 238e.

Workup

  1. customA 40 mL reaction
  2. temperatureThe mixture was gently heated until it
  3. customThe solvent was removed under reduced pressure
  4. customyielding the orange solid
  5. filtrationThe resulting solids were collected by filtration
  6. washwashed acetonitrile

Sources & evidence

ORD record
ord-9997a8772c6742029dce4630b7a17857
Source dataset
uspto-grants-2014_11
Patent number
US08877763B2

Reaction notes

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