Toluene → HCID 24941074, compound

HRID 1030243Notes

Reaction equation

HRID 1030243 reaction equation
[C:1]([CH:3]=[C:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[C:10](=[S:13])[NH:11][CH3:12])#N.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=[O:40].[Na+].[K+]>ClCCl>[CH:1]([CH:3]=[C:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[C:10](=[S:13])[NH:11][CH3:12])=[O:40]

Participants

6

Reactant 4

HCID 1140TolueneHCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 54056685HCID 54056685, compound

Product 1

HCID 24941074HCID 24941074, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (±)-2 -cyanomethylene-N-methyl-1-(pyrid-3 -yl}cyclohexane carbothioamide (1.3 g, 4.8 mmol) in dichloromethane (30 ml) was cooled to -20° C. and treated with a 1 M solution of diisobutylaluminium hydride in toluene (10.6 ml, 10.6 mmol). The mixture was allowed to warm to room temperature over 2 hours. Dichloromethane (50 ml) was added to the reaction mixture followed by an aqueous solution of Rochelle salt (sodium potassium tartrate) (50 ml). The layers were separated and the organic layer was washed with an aqueous solution of Rochelle salt (50 ml). The organic extract was dried over magnesium sulphate and concentrated in vacuo to give a crude gum which was purified by flash chromatography over silica gel, eluting with a 4:1 (v/v) mixture of ethyl acetate/hexane to give (±)-2 -formylmethylene-N-methyl-1-(pyrid-3 -yl)cyclohexane carbothioamide as a white foam (230 mg, 0.84 mmol);

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with an aqueous solution of Rochelle salt (50 ml)
  3. extractionThe organic extract
  4. dry with materialwas dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customto give a crude gum which
  7. customwas purified by flash chromatography over silica gel
  8. washeluting with a 4:1 (v/v) mixture of ethyl acetate/hexane

Sources & evidence

ORD record
ord-871e3118543b4dc7b52f40f4fce7e7c7
Source dataset
uspto-grants-1992_04
Patent number
US05104883

Reaction notes

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