Ethanol → HCID 19823821, compound

HRID 728263Notes

Reaction equation

HRID 728263 reaction equation
C1(C)C=CC(S([CH2:10][N+:11]#[C-])(=O)=O)=CC=1.[H-].[Na+].[CH2:16](O)[CH3:17].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2([CH:30]([N:37]([CH3:39])[CH3:38])[CH2:31][CH2:32][CH2:33]C(=O)C)[CH2:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1>CN(C)C=O.O1CCCC1.O>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2([CH:30]([N:37]([CH3:39])[CH3:38])[CH2:31][CH2:32][CH2:33][CH:16]([CH3:17])[C:10]#[N:11])[CH2:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 161915Tosylmethyl isocyanide2×HCID 19823883HCID 19823883, compound

Product 1

HCID 19823821HCID 19823821, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of p-toluenesulphonylmethylisocyanide sold under the trade name TosMIC (5 g) in dimethylformamide (10 ml) was added at 0° C. under argon over a period of 10 minutes to a stirred suspension of sodium hydride (3.6 g of a 50% dispersion in mineral oil) in dimethylformamide (30 ml). Ethanol (3.6 ml) was then added at 0° C. After 30 minutes a solution of 6-[1-(4-chlorophenyl)cyclobutyl]-6-dimethylaminohexan-2-one (6.11 g prepared in a similar manner to that described in Example 53) in tetrahydrofuran (50 ml) was added at 0° C. and the mixture stirred at ambient temperature for 16 hours. The reaction mixture was poured into water and the aqueous mixture extracted with ether. The extracts were washed, dried and evaporated to give an oil which was distilled on a Buchi Kugelrohr apparatus (150° C./0.35 mm). The distillate was dissolved in ether and treated with maleic acid to give a gum which was washed with ether and basified to give 6-[1-(4-chlorophenyl)cyclobutyl]-6-dimethylamino-2-methylhexanenitrile (mp 54°-56° C.)

Workup

  1. additionwas added at 0° C.
  2. extractionthe aqueous mixture extracted with ether
  3. washThe extracts were washed
  4. customdried
  5. customevaporated
  6. customto give an oil which
  7. distillationwas distilled on a Buchi Kugelrohr apparatus (150° C./0.35 mm)
  8. dissolutionThe distillate was dissolved in ether
  9. additiontreated with maleic acid
  10. customto give a gum which
  11. washwas washed with ether

Sources & evidence

ORD record
ord-2cd99f1e04d742c38a4683c186f9a8b8
Source dataset
uspto-grants-1991_09
Patent number
US05047432

Reaction notes

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