Reaction #65700

ord-ad0cc296182b433e88e7260edfb497f1

Reaction equation

Sc1ccccc1
Thiophenol
C1COCCOCCOCCOCCOCCO1.[C-]#N.[K+]
KCN 18-crown-6
O=C([O-])[O-].[K+].[K+]
potassium carbonate
[Cl-]
chloride
CC(CCl)CBr
1-bromo-3-chloro-2-methylpropane
→
CC1CCc2ccccc2SC1
2,3,4,5-tetrahydro-3-methyl-1-benzothiepine

Reactants

Sc1ccccc1
Thiophenol
C1COCCOCCOCCOCCOCCO1.[C-]#N.[K+]
KCN 18-crown-6
O=C([O-])[O-].[K+].[K+]
potassium carbonate
[Cl-]
chloride
—
polyphosphoric acid
CC(CCl)CBr
1-bromo-3-chloro-2-methylpropane

Reagents

None

Solvents

CC(C)=O
acetone
CC#N
acetonitrile

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Thiophenol was alkylated with 1-bromo-3-chloro-2-methylpropane in the presence of potassium carbonate (K2CO3) in acetone. The resulting primary chloride was lengthened by one carbon atom using KCN/18-crown-6 in acetonitrile. Basic hydrolysis, ring closure with polyphosphoric acid in analogy to Example 17(C) and Wolf-Kishner reduction according to Example 17(D) finally gave the required 2,3,4,5-tetrahydro-3-methyl-1-benzothiepine as a colorless oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05420273uspto-grants-1995_05