Triethylamine → (E)-2-(2-Chloromethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile
Reaction equation
C(C1N([CH2:14][C:15]2[CH:32]=[CH:31][C:18]3/[C:19](=[CH:28]/[C:29]#[N:30])/[C:20]4[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=4[CH2:22][CH2:23][C:17]=3[CH:16]=2)C2=NC(C)=CC(C)=C2N=1)C.C(N(CC)CC)C.CS([Cl:44])(=O)=O.[Cl-].[Li+]>C1COCC1.C(OCC)(=O)C>[Cl:44][CH2:14][C:15]1[CH:32]=[CH:31][C:18]2/[C:19](=[CH:28]/[C:29]#[N:30])/[C:20]3[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=3[CH2:22][CH2:23][C:17]=2[CH:16]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
(E)-(2-Hydroxymethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile (JP-B-2526005; 2.61 g, 10.0 mmol) was dissolved in THF (26 mL), triethylamine (2.09 mL, 15.0 mmol), methanesulfonyl chloride (1.16 mL, 15.0 mmol) and lithium chloride (0.636 g, 15.0 mmol) were added, and the mixture was stirred at 50° C. for 2 hr. Ethyl acetate was added to the mixture, and the organic layer was washed with brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Isopropyl ether (30 mL) was added to the obtained residue, and the mixture was filtered to give the title compound (2.59 g, 93%).
Workup
- washthe organic layer was washed with brine
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- additionIsopropyl ether (30 mL) was added to the obtained residue
- filtrationthe mixture was filtered
Sources & evidence
- ORD record
- ord-6cc7763fe7e14e8f8aeb4a31a5bd6eed
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08486980B2
Reaction notes
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