Toluene → HCID 57246350, compound

HRID 1030244Notes

Reaction equation

HRID 1030244 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][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)[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:44].[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][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10](=[S:13])[NH:11][CH3:12])=[O:44]

Participants

6

Reactant 4

HCID 1140TolueneHCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 54038574HCID 54038574, compound

Product 1

HCID 57246350HCID 57246350, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
10 °C

Procedure

A solution of (±)-2 -cyanomethylene-N-methyl-1-(quinolin-3 -yl)cyclohexane carbothioamide (1 g, 3.1 mmol) in dichloromethane (25 ml) was cooled to -20° C. and treated with a 1 M solution of diisobutylaluminium hydride in toluene (3.1 ml, 3.1 mmol). The mixture was allowed to warm to 10° C. over 90 mins. Dichloromethane (50 ml) was added to the reaction mixture followed by an aqueous solution of Rochelle salt (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 yield a yellow oil. Purification by flash chromatography over silica gel, eluting with a 1:1 (v/v) mixture of ethyl acetate/hexane yielded (±)-2 -formylmethylene-N-methyl-1-(quinolin-3 -yl)cyclohexane carbothioamide (300 mg, 0.93 mmol) as a pale yellow solid, m.p. 149°-151° C.;

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 yield a yellow oil
  7. customPurification by flash chromatography over silica gel
  8. washeluting with a 1:1 (v/v) mixture of ethyl acetate/hexane

Sources & evidence

ORD record
ord-43f4f6305a1d479a83716228893709e2
Source dataset
uspto-grants-1992_04
Patent number
US05104883

Reaction notes

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