Diethyl Oxalate → Stk848494

HRID 26468

Reaction equation

HRID 26468 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[C:11](OCC)(=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13]>>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[NH:1][C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

3

Reactant 2

HCID 7268Diethyl OxalateHCID 8706Benzo(d)thiazol-2-amine

Product 1

HCID 1929314Stk848494Yield 44%

Procedure

A mixture of 2-aminobenzothiazole (5.0 g., 0.033 mol) and diethyl oxalate (50 ml.) is heated at reflux for 2.5 hours. A white solid precipitates from the cooled reaction mixture. The solid is recrystallized from ethanol (with a hot filtration) to give the desired product (3.72 g., m.p. 185°-186°, 44%).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2.5 hours
  3. customA white solid precipitates from the cooled reaction mixture
  4. customThe solid is recrystallized from ethanol (
  5. filtrationwith a hot filtration)

Sources & evidence

ORD record
ord-af901c900f3c41d296dc87a9b6bb9c7e
Source dataset
uspto-grants-1979_04
Patent number
US04150140

Linked notes

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