Water → HCID 54539209, compound

HRID 581919Notes

Reaction equation

HRID 581919 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[NH2:13][C:14]1[CH:15]=[C:16]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][N:21]=2)[CH:17]=[CH:18][CH:19]=1.[H-].[Na+].O>C1COCC1>[N:23]1[CH:24]=[CH:25][C:20]([C:16]2[CH:15]=[C:14]([NH:13][C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=3[N+:10]([O-:12])=[O:11])[CH:19]=[CH:18][CH:17]=2)=[N:21][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 24758Sodium hydrideHCID 124561713-(Pyrimidin-4-yl)aniline

Product 1

HCID 54539209HCID 54539209, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-chloro-3-nitrobenzonitril (5.5 g, 30 mmol) and (58) (5.1 g, 30 mmol) in THF (120 ml) was added sodium hydride (2.3 g, 50% suspension in mineral oil). After stirring at room temperature for 2 days, the mixture was poured into water and extracted with CH2Cl2. The extract was concentrated under reduced pressure and the residue was triturated with diethylether to yield crystalline (59) (9.2 g, 96%).

Workup

  1. extractionextracted with CH2Cl2
  2. concentrationThe extract was concentrated under reduced pressure
  3. customthe residue was triturated with diethylether

Sources & evidence

ORD record
ord-d0b093f34e9d4a2097649974f295b5e1
Source dataset
uspto-grants-1999_07
Patent number
US05922725

Reaction notes

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