1-(Bromomethyl)-2-chloro-4-(methylsulfonyl)benzene → HCID 68661918, compound

HRID 1260859Notes

Reaction equation

HRID 1260859 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[Br:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][C:15]=1[Cl:24]>CN(C)C=O.C(OCC)(=O)C>[BrH:12].[Cl:11][C:8]1[CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:2](=[NH:1])[N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:21])=[O:22])=[CH:16][C:15]=2[Cl:24])[CH:9]=1

Participants

5

Reactant 2

HCID 27610831-(Bromomethyl)-2-chloro-4-(methylsulfonyl)benzeneHCID 668768832-Amino-5-chloronicotinamide

Product 1

HCID 68661918HCID 68661918, compoundYield 22.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added 1-(bromomethyl)-2-chloro-4-(methylsulfonyl)benzene (0.37 g), and the mixture was stirred at 100° C. for 14 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (90 mg).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with ethyl acetate
  3. customThe obtained precipitate was recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-a66520230af347cd983d91a6d4a4813c
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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