Acetic Acid → HCID 135984214, compound

HRID 1292534Notes

Reaction equation

HRID 1292534 reaction equation
C[O:2][C:3]1[CH:23]=[CH:22][C:6]2[C:7]([CH:10]3[CH2:15][NH:14][CH2:13][CH2:12][N:11]3[C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[N:8][O:9][C:5]=2[CH:4]=1.C(O)(=O)C>CN(C=O)C>[N:19]1[CH:18]=[CH:17][C:16]([N:11]2[CH2:12][CH2:13][NH:14][CH2:15][CH:10]2[C:7]2[C:6]3[CH:22]=[CH:23][C:3]([OH:2])=[CH:4][C:5]=3[O:9][N:8]=2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 53755177HCID 53755177, compound

Product 1

HCID 135984214HCID 135984214, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 6-methoxy-3-[1-(4-pyridyl)piperazinyl]-1,2-benzisoxazole (1.75 g) and sodium ethylthiolate (0.79 g) in DMF (30 ml) was heated to 105°-107° C. under N2 for 3 hours. TLC (silica gel 30% MeOH/CH2Cl2) showed no presence of starting material. Glacial acetic acid (5 ml) was added and the solvent was removed in vacuo. The residue was flash chromatographed (silica gel) eluting with 10% MeOH/CH2Cl2 to afford 1.1 g of material. The material was further purified through recrystallization from pyridine to afford 1.0 g of the product, m.p.>250° C.

Workup

  1. customthe solvent was removed in vacuo
  2. customchromatographed (silica gel)
  3. washeluting with 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-a9cac98e55194e23bc15c9d04fb1c112
Source dataset
uspto-grants-1998_05
Patent number
US05756754

Reaction notes

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