4-Methylbenzaldehyde → HCID 58392144, compound

HRID 561431Notes

Reaction equation

HRID 561431 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C:11]1([CH3:19])[O:18][C:16](=[O:17])[CH2:15][C:13](=[O:14])[O:12]1.[CH3:20][S:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]2[C:31]=1[NH:30][CH:29]=[CH:28]2>C(#N)C.N1CCCC1C(O)=O>[CH3:10][C:11]1([CH3:19])[O:18][C:16](=[O:17])[CH:15]([CH:6]([C:5]2[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][CH:4]=2)[C:28]2[C:27]3[C:31](=[C:23]([CH2:22][S:21][CH3:20])[CH:24]=[CH:25][CH:26]=3)[NH:30][CH:29]=2)[C:13](=[O:14])[O:12]1

Participants

6

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 58392144HCID 58392144, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 614proline dl-formCatalystHCID 6342AcetonitrileSolvent

Procedure

1.28 g (10.7 mmol) of 4-methylbenzaldehyde, 1.54 g (10.7 mmol) of Meldrum's acid and 58.0 mg (0.51 mmol) of D,L-proline were added to a solution of 2.00 g (10.2 mmol) of the compound from Example 8A in 80 ml of acetonitrile. The reaction mixture was stirred at RT overnight. It was concentrated, and the residue was taken up in ethyl acetate, washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution and water, dried over magnesium sulfate, filtered and concentrated. 4.34 g of the title compound were obtained and were reacted without further purification.

Workup

  1. concentrationIt was concentrated
  2. washwashed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution and water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1cfa686502fd4fa79ba2944d82516263
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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