3,4-Dichlorobenzaldehyde → HCID 18789260, compound

HRID 1106631Notes

Reaction equation

HRID 1106631 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.[CH3:36][O:37][C:38]1[CH:48]=[CH:47][C:41]([CH2:42][S:43][C:44](=[NH:46])[NH2:45])=[CH:40][CH:39]=1.C(=O)([O-])O.[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:46][C:44]([S:43][CH2:42][C:41]3[CH:47]=[CH:48][C:38]([O:37][CH3:36])=[CH:39][CH:40]=3)=[N:45]2)[CH:32]=[CH:33][C:34]=1[Cl:35]

Participants

6

Reactant 4

HCID 227103,4-DichlorobenzaldehydeHCID 415139(4-Methoxyphenyl)methyl carbamimidothioateHCID 516892Sodium BicarbonateHCID 220055123-Phenylpropyl 4-(2-(1-piperidinyl)ethoxy)acetoacetate

Product 1

HCID 18789260HCID 18789260, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-phenylpropyl 4-(2-(1-piperidinyl)ethoxy)acetoacetate (1.0 g, 2.88 mmol), 3,4-dichlorobenzaldehyde (0.60 g, 3.45 mmol), 2-(4-methoxybenzyl)isothiourea (0.80 g, 3.45 mmol) and sodium hydrogen carbonate (0.29 g, 3.45 mmol) was stirred in N,N-dimethylformamide (10 mL) for 6 days at room temperature, then heated to 50° C. for 7 days. 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 (0.50 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 682/684 [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-26a4fb1d35d143e7bbcf9a7b84c018b3
Source dataset
uspto-grants-2000_05
Patent number
US06057332

Reaction notes

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