p-Tolunitrile → HCID 59384156, compound

HRID 2356594Notes

Reaction equation

HRID 2356594 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)=[NH:13])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[O:21]1[C:26]2C=CC(N)=[CH:30][C:25]=2OCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1(C)C=CC(C#N)=CC=1.[O:51]1CCCC1>[Cl-].[Na+].O.ClCCl>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([N:11]3[CH:30]=[C:25]([C:26]([OH:51])=[O:21])[N:13]=[C:12]3[C:14]3[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 7724p-TolunitrileHCID 8028Tetrahydrofuran2×HCID 891481,4-Benzodioxan-6-ylamineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 178425626HCID 178425626, compound

Product 1

HCID 59384156HCID 59384156, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

N-(2,3-Dihydro-1,4-benzodioxin-6-yl)-4-methylbenzenecarboxamidine To a solution of 0.605 g (4.0 mmol) of 1,4-benzodioxan-6-amine in 5 mL of tetrahydrofuran at ambient temperature was added 2.2 ml (4.4 mmol) of 2.0 M (in tetrahydrofuran) sodium bis(trimethylsilyl)amide 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 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 25 mL of dichloromethane (25 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to yield the title compound as brown crystalline solid, which was used without further purification. LC/MS 269.2 (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 25 mL of 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-398dc48fff01402ba0e428decceee10d
Source dataset
uspto-grants-2010_07
Patent number
US07759352B2

Reaction notes

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