Potassium Carbonate → HCID 14987128, compound

HRID 892688Notes

Reaction equation

HRID 892688 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13](Cl)=[O:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[NH2:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:20]1([CH2:19][CH2:18][CH2:17][NH:16][C:13]([C:11]2[O:12][C:8]([C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)=[CH:9][CH:10]=2)=[O:14])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 61055N-(3-Aminopropyl)morpholineHCID 4769304HCID 4769304, compound

Product 1

HCID 14987128HCID 14987128, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4.06 g of 5-(4-bromphenyl)-2-furancarboxylic acid chloride and 2.55 g of N-(3-aminopropyl)morpholine is refluxed 6 hr with 3.0 g of anhydrous potassium carbonate in 50 ml of acetonitrile. The mixture is allowed to stir at room temperature overnight. Solvents are then evaporated and the residue is triturated with ethyl ether followed by evaporation again. This process is repeated several times. A solution of the residue in ethyl ether is allowed to stand overnight whereupon crystals are formed. After three recrystallizations from ethyl acetate, the product, 2.47 g (37.5%), melts at 83°-100° The CI and EI mass spec. are consistent with the proposed structure. The latter showed M+ =393.

Workup

  1. customSolvents are then evaporated
  2. customthe residue is triturated with ethyl ether
  3. customfollowed by evaporation again
  4. waitto stand overnight whereupon crystals
  5. customare formed
  6. customAfter three recrystallizations from ethyl acetate

Sources & evidence

ORD record
ord-80f65852c13848b2ad2d7794cb623475
Source dataset
uspto-grants-1992_06
Patent number
US05118708

Reaction notes

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