Water → HCID 54539209, compound

HRID 581967Notes

Reaction equation

HRID 581967 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=1[N+:23]([O-:25])=[O:24].[H-].[Na+].O>C1COCC1>[N:11]1[CH:12]=[CH:13][C:8]([C:4]2[CH:3]=[C:2]([NH:1][C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=3[N+:23]([O-:25])=[O:24])[CH:7]=[CH:6][CH:5]=2)=[N:9][CH:10]=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 (37) (5.5 g, 30 mmol) and 4-chloro-3-nitro-benzonitril (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 diethyl ether to yield crystalline (38) (9.2 g, 96%).

Workup

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

Sources & evidence

ORD record
ord-903aff3ef80546c8a4a05d3f923d6573
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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