Dichloromethane → HCID 178511896, compound

HRID 1010612Notes

Reaction equation

HRID 1010612 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[F:22][C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1.ClCCl>O1CCCC1.[Cl-].[Na+].O>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH:11][C:27]([C:26]3[CH:29]=[CH:30][C:23]([F:22])=[CH:24][CH:25]=3)=[NH:28])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 145174-FluorobenzonitrileHCID 891481,4-Benzodioxan-6-ylamineHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 178511896HCID 178511896, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2.39 g (15.8 mmol) of 1,4-benzodioxan-6-amine in 30 mL of tetrahydrofuran at ambient temperature was added 8.7 mL (17.4 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 added 1.91 g (15.8 mmol) of 4-fluorobenzonitrile all at once. The resulting mixture was stirred at ambient temperature overnight and then poured into brine (50 mL) and dichloromethane (150 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (50 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 273.2 (M+1).

Workup

  1. stirringThe resulting mixture was stirred at ambient temperature overnight
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane (50 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf6fb552ba344c968d2b31a8c0a0d5d7
Source dataset
uspto-grants-2011_07
Patent number
US07977339B2

Reaction notes

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