Dichloromethane → HCID 178466607, compound

HRID 1010600Notes

Reaction equation

HRID 1010600 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:11]([O:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17])[CH3:12].[C:21]1([CH3:29])[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=1.ClCCl>O1CCCC1.[Cl-].[Na+].O>[CH2:11]([O:13][C:14]1[CH:15]=[C:16]([NH:17][C:27]([C:24]2[CH:25]=[CH:26][C:21]([CH3:29])=[CH:22][CH:23]=2)=[NH:28])[CH:18]=[CH:19][CH:20]=1)[CH3:12]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7724p-TolunitrileHCID 121203-EthoxyanilineHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 178466607HCID 178466607, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2.2 mL (4.4 mmol) of 2.0 M (in tetrahydrofuran) sodium bis(trimethylsilyl)amide in 5.0 mL of tetrahydrofuran at ambient temperature was added 0.52 mL (4.0 mmol) of 3-ethoxyaniline and the resulting solution was stirred for 20 min. To this reaction mixture was slowly added a solution of 0.47 g (4.0 mmol) of p-tolunitrile in 2.0 mL of tetrahydrofuran. The resulting mixture was stirred at ambient temperature for 5 hrs and then poured into brine (25 mL) and dichloromethane (50 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (25 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to yield the title compound as yellow solid which was used without further purification. LC/MS 255.2 (M+1).

Workup

  1. stirringThe resulting mixture was stirred at ambient temperature for 5 hrs
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane (25 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e770d567576f4d07a34a84da709b14a3
Source dataset
uspto-grants-2011_07
Patent number
US07977339B2

Reaction notes

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