Sodium Acetate → HCID 14277637, compound

HRID 35535Notes

Reaction equation

HRID 35535 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]2[C:12]([OH:13])=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:10][C:9]=2[N:20]=1)([CH3:4])[CH3:3].[C:21]([O-])(=[O:23])[CH3:22].[Na+]>C(OC(=O)C)(=O)C>[C:21]([O:13][C:12]1[C:8]2[CH:7]=[CH:6][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[N:20][C:9]=2[S:10][C:11]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 14277636HCID 14277636, compound

Product 1

HCID 14277637HCID 14277637, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 1.42 g (5 mmol) of 6(1,1-dimethylethyl)-3-hydroxy-2-phenyl-7-azabenzo[b]thiophene and 1.42 g sodium acetate in 20 mL of acetic anhydride was heated at reflux for 1 hour. The solution was concentrated and the residue was partitioned between ether and water. The ether layer was washed with sodium bicarbonate solution and brine, dried and concentrated. The residue was crystallized from ether-hexane to afford 1.49 g (91%) of fine white needles, m.p. 128°-9° C.

Workup

  1. temperatureat reflux for 1 hour
  2. concentrationThe solution was concentrated
  3. customthe residue was partitioned between ether and water
  4. washThe ether layer was washed with sodium bicarbonate solution and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was crystallized from ether-hexane

Sources & evidence

ORD record
ord-38d8ef021ab142608c8c21a9cc45f129
Source dataset
uspto-grants-1988_08
Patent number
US04767766

Reaction notes

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