Mercaptoacetonitrile → 11-Cyanomethylthio-2-(quinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine

HRID 232881Notes

Reaction equation

HRID 232881 reaction equation
[SH:1][CH2:2][C:3]#[N:4].O[CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][O:9][C:8]2[CH:17]=[CH:18][C:19]([O:21][CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)=[CH:20][C:7]1=2>FC(F)(F)C(O)=O.C(Cl)Cl.C(OCC)(=O)C>[C:3]([CH2:2][S:1][CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][O:9][C:8]2[CH:17]=[CH:18][C:19]([O:21][CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)=[CH:20][C:7]1=2)#[N:4]

Participants

6

Reactant 2

HCID 4346655MercaptoacetonitrileHCID 2335916711-Hydroxy-2-(quinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine

Product 1

HCID 2335915911-Cyanomethylthio-2-(quinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepineYield 48.2%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under ice cooling and stirring, 0.44 g of mercaptoacetonitrile was added to 2.22 g of 11-hydroxy-2-(quinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine obtained in Reference example 45 dissolved in a mixed solution of 20 ml of trifluoroacetic acid and 10 ml of methylene chloride and the mixture was stirred at the same temperature for 1.5 hours. The residue obtained by condensing the reaction mixture under reduced pressure was dissolved in ethyl acetate and the organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated saline solution and dried over anhydrous sodium sulfate. The viscous residue obtained by removing the solvent was crystallized from diethyl ether to obtain 1.23 g of the title compound.

Workup

  1. customobtained in Reference example 45
  2. stirringthe mixture was stirred at the same temperature for 1.5 hours
  3. customThe residue obtained by condensing the reaction mixture under reduced pressure
  4. washthe organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution
  5. dry with materiala saturated saline solution and dried over anhydrous sodium sulfate
  6. customThe viscous residue obtained
  7. customby removing the solvent
  8. customwas crystallized from diethyl ether

Sources & evidence

ORD record
ord-90afd8ef592641ed97a12afedabac117
Source dataset
uspto-grants-1997_01
Patent number
US05591752

Reaction notes

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