N-bromobutanimide → HCID 86704193, compound

HRID 1497655Notes

Reaction equation

HRID 1497655 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[C:8]([F:28])=[C:9]([N:13]([CH2:25][O:26][CH3:27])[S:14]([C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=3[F:24])(=[O:16])=[O:15])[CH:10]=[CH:11][CH:12]=2)[N:6]=1.[Br:29]N1C(=O)CCC1=O>C(Cl)Cl>[NH2:1][C:2]1[S:3][C:4]([Br:29])=[C:5]([C:7]2[C:8]([F:28])=[C:9]([N:13]([CH2:25][O:26][CH3:27])[S:14]([C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=3[F:24])(=[O:16])=[O:15])[CH:10]=[CH:11][CH:12]=2)[N:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86704191HCID 86704191, compound

Product 1

HCID 86704193HCID 86704193, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.26 g (2.94 mmol) of N-[3-(2-amino-1,3-thiazol-4-yl)-2-fluorophenyl]-2,5-difluoro-N-(methoxymethyl)-benzenesulfonamide were dissolved in 30 ml of dry DCM and 523 mg (2.94 mmol) of N-bromosuccinimide were added. The resulting solution was stirred at r.t. for 30 min. The mixture was diluted with the same solvent and washed with aqueous NaHCO3. The organic layer was dried over Na2SO4 and evaporated. The residue was triturated with diisopropyl ether and filtered to afford 1.4 g (93%) of the title compound.

Workup

  1. additionThe mixture was diluted with the same solvent
  2. washwashed with aqueous NaHCO3
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated
  5. customThe residue was triturated with diisopropyl ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-16504d8d7b39428b9f79248c6ef49c61
Source dataset
uspto-grants-2015_12
Patent number
US09199979B2

Reaction notes

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