3,4-Dichlorobenzaldehyde → HCID 9851145, compound

HRID 1106630Notes

Reaction equation

HRID 1106630 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][CH2:10][C:11](=O)[CH2:12][C:13]([O:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH:30]=O.S(O)(O)(=O)=O.[CH3:41][S:42][C:43](=[NH:45])[NH2:44].C([O-])(=O)C.[Na+]>CN(C)C=O>[Cl:26][C:27]1[CH:28]=[C:29]([CH:30]2[C:12]([C:13]([O:15][CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:14])=[C:11]([CH2:10][O:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[NH:45][C:43]([S:42][CH3:41])=[N:44]2)[CH:32]=[CH:33][C:34]=1[Cl:35]

Participants

6

Reactant 4

HCID 227103,4-DichlorobenzaldehydeHCID 752702-Methyl-2-thiopseudourea sulfateHCID 517045Sodium AcetateHCID 220055123-Phenylpropyl 4-(2-(1-piperidinyl)ethoxy)acetoacetate

Product 1

HCID 9851145HCID 9851145, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-phenylpropyl 4-(2-(1-piperidinyl)ethoxy)acetoacetate (10.6 g, 30.6 mmol), 3,4-dichlorobenzaldehyde (5.9 g, 34.0 mmol), 2-methyl-2-thiopseudourea sulfate (6.15 g, 22.1 mmol) and sodium acetate (2.78 g, 34.0 mmol) was stirred in N,N-dimethylformamide (50 mL) for 4 days at room temperature, then heated to 60° C. for 24 h. The DMF was removed in vacuo and ethyl acetate was added to the residue. The precipitate was removed by filtration and the filtrate was washed with water, sodium hydrogen carbonate solution and brine, dried and evaporated to yield an oil. This oil was further purified by flash chromatography to give the title compound (1.3 g) as an oil. The oil can be converted into a mono or dihydrochloride salt, by dissolution in ether and addition of one or two equivalents of hydrogen chloride. Electrospray MSm /z 576/578 [M+H]+.

Workup

  1. customThe DMF was removed in vacuo and ethyl acetate
  2. additionwas added to the residue
  3. customThe precipitate was removed by filtration
  4. washthe filtrate was washed with water, sodium hydrogen carbonate solution and brine
  5. customdried
  6. customevaporated
  7. customto yield an oil
  8. customThis oil was further purified by flash chromatography

Sources & evidence

ORD record
ord-8b7a925018cd4d06a61c672972a64284
Source dataset
uspto-grants-2000_05
Patent number
US06057332

Reaction notes

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