Oxalic Acid → HCID 22666389, compound

HRID 1007885Notes

Reaction equation

HRID 1007885 reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[CH2:4][CH2:5][O:6][CH2:7][CH2:8][C:9]1[C:17]([F:18])=[CH:16][C:12]2[S:13][CH:14]=[CH:15][C:11]=2[CH:10]=1)[CH3:2].[C:21]([OH:26])(=[O:25])[C:22]([OH:24])=[O:23]>C(OCC)(=O)C.C(OC(C)C)(C)C>[C:21]([OH:26])(=[O:25])[C:22]([OH:24])=[O:23].[CH2:19]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][CH2:7][CH2:8][C:9]1[C:17]([F:18])=[CH:16][C:12]2[S:13][CH:14]=[CH:15][C:11]=2[CH:10]=1)[CH3:20]

Participants

5

Reactant 2

HCID 971Oxalic AcidHCID 22666304HCID 22666304, compound

Product 1

HCID 22666389HCID 22666389, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 7914Diisopropyl EtherSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

In 2.5 mL of ethyl acetate is dissolved 0.90 g of N,N-diethyl-N-{2-[2-(6-fluorobenzo[b]thiophen-5-yl)ethoxy]ethyl}-amine, to which is added 2 ml of a solution of 0.27 g of oxalic acid in ethyl acetate. The resulting mixture is stirred at ambient temperature for 2 hours. The reaction mixture is diluted with 10 mL of diisopropyl ether, and the resulting crystalline precipitate is collected by filtration, washed with diisopropyl ether and dried. Thus, 0.83 g of N,N-diethyl-N-{2-[2-(6-fluorobenzo[b]thiophen-5-yl)ethoxy]ethyl}amine oxalate is obtained.

Workup

  1. filtrationthe resulting crystalline precipitate is collected by filtration
  2. washwashed with diisopropyl ether
  3. customdried

Sources & evidence

ORD record
ord-99dd6fe0890641fc9259558353ab7507
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

Loading…