Chlorosuccinimide → HCID 58259901, compound

HRID 1020206Notes

Reaction equation

HRID 1020206 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][N:12]([CH3:18])[C:11](=[O:19])[CH:10]=2)=[C:4]([F:20])[CH:3]=1.FC1C=C(I)C=CC=1NC1C([N+]([O-])=O)=CNC(=O)C=1.C1C(=O)N([Cl:47])C(=O)C1>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][N:12]([CH3:18])[C:11](=[O:19])[C:10]=2[Cl:47])=[C:4]([F:20])[CH:3]=1

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 57438270HCID 57438270, compoundHCID 58259902HCID 58259902, compound

Product 1

HCID 58259901HCID 58259901, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 4-(4-Bromo-2-fluoro-phenylamino)-1-methyl-5-nitro-1H-pyridin-2-one (451 mg, 1.323 mol), synthesized using the same procedures as for the synthesis of 4-(2-Fluoro-4-iodophenylamino)-5-nitropyridin-2(1H)-one, and NCS (286 mg, 2.14 mmol) in dry DMF (13 mL) was heated to 50° C. The solution became clear in 5 minutes, and the solution turned into light orange. The heating was continued over the 48 hours. At this time, LC/MS indicated there was 77% of the title product in the reaction mixture. The heating temperature was then raised to 70° C. and kept at that temperature for additional 4 hours. Water was added until the yellow precipitate formed. The stirring was continued at r.t. for 30 min. The precipitate was then filtered, washed with water (5 mL) and dried under high vacuum overnight. The title compound was used for the next reaction without further purification. (424 mg, 85% yield).

Workup

  1. customsynthesized
  2. customwas continued over the 48 hours

Sources & evidence

ORD record
ord-1a21597301fc4ba0bdc1854978950da1
Source dataset
uspto-grants-2014_05
Patent number
US08716318B2

Reaction notes

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